Reducing JPEG image size - jaggies in InDesign CC and Photoshop CC

I have a high-res jpeg, 600ppi, 11 inches by 6.603 inches. The image is 4.21 MB, so there's plenty of data.
I need to make it smaller to go into an InDesign document for print. I've been noticing this issue for awhile with CC. Recently I downsized a JPEG of line art in Photoshop for a poster, and it looked just awful.
When I reduce the size to 300ppi, and 4" wide, bicubic sharper, I'm noticing that diagonals especially look really jaggy. The smaller I go, the worse the jaggies are. This is counterintuitive, because I'm reducing the size of the image.
I have the Display Performance set to high-quality, with Allow Object-Level Display settings checked.
When I place the CMYK reduced-size JPEG onto the page, the diagonals look jaggy. I thought it was a monitor issue, and that is contributing to it, but when I print out the page on my printer, the diagonals are still kind of jaggy. I tried placing a TIFF, and oh, my, that was twice as bad. I tried placing a PDF. Ugh.
I've tried reducing the image to the exact size in Photoshop so I don't have to scale it in ID, then placing the image, and still jaggies.
I've tried taking that image and dragging it from Bridge into the ID File. Still jaggies.
I did print the image out directly from Photoshop at the smaller size, and it looks perfect.
What could be happening? Is there a way to fix it? I'm working on a bunch of print work with some really nice photos in them (for a couple of real estate clients), and I'm afraid when the collateral gets printed, it's going to look like crap.

Recently I downsized a JPEG of line art in Photoshop for a poster, and it looked just awful.
When I reduce the size to 300ppi, and 4" wide,
If it's really line art (no gray values) then 300ppi isn't enough. Line art needs to be closer to the output resolution (800-1200 ppi), and shouldn't be saved as JPEG.

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    08/21/14 09:27:20:532 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign/Version 10.0". Check and correct folder & parent directory permissions and then try again.(Seq 5)
    08/21/14 09:27:20:532 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 5)
    08/21/14 09:27:20:532 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Library/Application Support/Adobe/HelpCfg/en_GB". Check and correct folder & parent directory permissions and then try again.(Seq 6)
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    08/21/14 09:27:20:532 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEPServiceManager4/Adobe/AdobePatchFiles". Check and correct folder & parent directory permissions and then try again.(Seq 7)
    08/21/14 09:27:20:532 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 7)
    08/21/14 09:27:20:532 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEPServiceManager4/Adobe". Check and correct folder & parent directory permissions and then try again.(Seq 8)
    08/21/14 09:27:20:532 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 8)
    08/21/14 09:27:20:532 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEP/extensions". Check and correct folder & parent directory permissions and then try again.(Seq 9)
    08/21/14 09:27:20:532 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 9)
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    08/21/14 09:27:20:532 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 11)
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    08/21/14 09:27:20:533 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014". Check and correct folder & parent directory permissions and then try again.(Seq 18)
    08/21/14 09:27:20:533 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 18)
    08/21/14 09:27:20:533 | [ERROR] |  | OOBE | DE |  |  |  | 25152 | DF037: Unable to delete directory "/Applications/Adobe". Check and correct folder & parent directory permissions and then try again.(Seq 19)
    08/21/14 09:27:20:533 | [WARN] |  | OOBE | DE |  |  |  | 25152 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 19)
    08/21/14 09:27:20:533 | [INFO] |  | OOBE | DE |  |  |  | 25152 | Completing un-installation for payload at /Library/Application Support/Adobe/Uninstall/CommonUninstall.db
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    08/21/14 09:27:20:623 | [INFO] |  | OOBE | DE |  |  |  | 24018 | *=*=*=*=*=*=*=*=*=*=*=*=*=*=*=* Operation complete. Setting status: 0 =*=*=*=*=*=*=*=*=*=*=*=*=*
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    10/22/14 11:18:46:938 | [INFO] |  | OOBE | DE |  |  |  | 77654 | UninstallSeq property not found in database
    10/22/14 11:18:46:938 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Users/MikeTessersComputer/Library/Preferences/Adobe/dynamiclinkmediaserver". Check and correct folder & parent directory permissions and then try again.(Seq 1)
    10/22/14 11:18:46:938 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 1)
    10/22/14 11:18:46:938 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Users/MikeTessersComputer/Library/Preferences/Adobe InDesign". Check and correct folder & parent directory permissions and then try again.(Seq 2)
    10/22/14 11:18:46:938 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 2)
    10/22/14 11:18:46:938 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe". Check and correct folder & parent directory permissions and then try again.(Seq 3)
    10/22/14 11:18:46:938 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 3)
    10/22/14 11:18:46:938 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/Startup Scripts CC/Adobe Photoshop". Check and correct folder & parent directory permissions and then try again.(Seq 4)
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    10/22/14 11:18:46:938 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign/Version 9.0/en_US". Check and correct folder & parent directory permissions and then try again.(Seq 6)
    10/22/14 11:18:46:938 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 6)
    10/22/14 11:18:46:938 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign/Version 9.0". Check and correct folder & parent directory permissions and then try again.(Seq 7)
    10/22/14 11:18:46:938 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 7)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign/Version 10.0/en_GB/Extensions". Check and correct folder & parent directory permissions and then try again.(Seq 8)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 8)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign/Version 10.0/en_GB". Check and correct folder & parent directory permissions and then try again.(Seq 9)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 9)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign/Version 10.0". Check and correct folder & parent directory permissions and then try again.(Seq 10)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 10)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/InDesign". Check and correct folder & parent directory permissions and then try again.(Seq 11)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 11)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/HelpCfg/ro_RO". Check and correct folder & parent directory permissions and then try again.(Seq 12)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 12)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/HelpCfg/en_GB". Check and correct folder & parent directory permissions and then try again.(Seq 13)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 13)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/HelpCfg/el_GR". Check and correct folder & parent directory permissions and then try again.(Seq 14)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 14)
    10/22/14 11:18:46:939 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEPServiceManager4/Adobe/AdobePatchFiles". Check and correct folder & parent directory permissions and then try again.(Seq 15)
    10/22/14 11:18:46:939 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 15)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEPServiceManager4/Adobe". Check and correct folder & parent directory permissions and then try again.(Seq 16)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 16)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEP/extensions". Check and correct folder & parent directory permissions and then try again.(Seq 17)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 17)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/CEP". Check and correct folder & parent directory permissions and then try again.(Seq 18)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 18)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/Adobe/AdobePatchFiles". Check and correct folder & parent directory permissions and then try again.(Seq 19)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 19)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Library/Application Support/Adobe/Adobe". Check and correct folder & parent directory permissions and then try again.(Seq 20)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 20)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Photoshop CC 2014/Plug-ins". Check and correct folder & parent directory permissions and then try again.(Seq 21)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 21)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Photoshop CC 2014". Check and correct folder & parent directory permissions and then try again.(Seq 22)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 22)
    10/22/14 11:18:46:940 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe InDesign CC 2014/Plug-Ins". Check and correct folder & parent directory permissions and then try again.(Seq 23)
    10/22/14 11:18:46:940 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 23)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe InDesign CC 2014/Plug-Ins". Check and correct folder & parent directory permissions and then try again.(Seq 24)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 24)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe InDesign CC 2014". Check and correct folder & parent directory permissions and then try again.(Seq 25)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 25)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe InDesign CC 2014". Check and correct folder & parent directory permissions and then try again.(Seq 26)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 26)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014/Plug-ins.localized/Extensions.localized". Check and correct folder & parent directory permissions and then try again.(Seq 27)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 27)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014/Plug-ins.localized/Extensions.localized". Check and correct folder & parent directory permissions and then try again.(Seq 28)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 28)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014/Plug-ins.localized". Check and correct folder & parent directory permissions and then try again.(Seq 29)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 29)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014/Plug-ins.localized". Check and correct folder & parent directory permissions and then try again.(Seq 30)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 30)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014". Check and correct folder & parent directory permissions and then try again.(Seq 31)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 31)
    10/22/14 11:18:46:941 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe Illustrator CC 2014". Check and correct folder & parent directory permissions and then try again.(Seq 32)
    10/22/14 11:18:46:941 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 32)
    10/22/14 11:18:46:942 | [ERROR] |  | OOBE | DE |  |  |  | 77654 | DF037: Unable to delete directory "/Applications/Adobe". Check and correct folder & parent directory permissions and then try again.(Seq 33)
    10/22/14 11:18:46:942 | [WARN] |  | OOBE | DE |  |  |  | 77654 | DW063: Command ARKDeleteDirectoryCommand failed.(Seq 33)
    10/22/14 11:18:46:942 | [INFO] |  | OOBE | DE |  |  |  | 77654 | Completing un-installation for payload at /Library/Application Support/Adobe/Uninstall/CommonUninstall.db
    10/22/14 11:18:46:942 | [INFO] |  | OOBE | DE |  |  |  | 77654 | Physical payload uninstall result:0
    10/22/14 11:18:47:030 | [INFO] |  | OOBE | DE |  |  |  | 77365 | *=*=*=*=*=*=*=*=*=*=*=*=*=*=*=* Operation complete. Setting status: 0

  • Indesign cs5 and photoshop cs5 preferences installed as one.

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