Macbook pro to macbook air plus upgrade to lion and moving to cloud -- help!

So, I'm getting a new macbook air and I need to transfer stuff (apps, software, data, music, photos, etc.) from my macbook pro (a 2008 unibody w/a full hard drive that's got twice the storage of the air).
Should I upgrade the pro from OS 10.6.8 to lion first?
Should I move stuff to the iCloud first?
Whould I move my media (music, movies, TV shows, photos) to a hard drive first?
I'm clearly nervous about the best order of operations here so that I don't lose any of my data & media, and so I have the least awful transition experience. In the past, I've always upgraded to systems with *larger* hard drives so moving to a system with much less storage is freaking me out.
Thanks for your help!

I took the conservative route when I migrated to the MBair.  I made a clone of my source machine, booted that and tailored it down to what I wanted on the MBair.  I left the original machine alone (with plenty of backups).
Then when I received the MBair, I connect my tailored, external disk clone and used that when setup assistant asked if I wanted to migrate another Mac to the MBair.
Regards,
Captfred

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    lidwake              1
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    1/05/2015 9:49:34.852 am GoogleSoftwareUpdateAgent[11054]: 2015-05-01 09:49:34.163 GoogleSoftwareUpdateAgent[11054/0xa0c2f1d4] [lvl=2] -[KSAgentApp setupLoggerOutput] Agent settings: <KSAgentSettings:0x5098d0 bundleID=com.google.Keystone.Agent lastCheck=2015-04-30 04:24:22 +0000 checkInterval=18000.000000 uiDisplayInterval=604800.000000 sleepInterval=1800.000000 jitterInterval=900 maxRunInterval=0.000000 isConsoleUser=1 ticketStorePath=/Users/phil/Library/Google/GoogleSoftwareUpdate/TicketStore/Key stone.ticketstore runMode=3 daemonUpdateEngineBrokerServiceName=com.google.Keystone.Daemon.UpdateEngine daemonAdministrationServiceName=com.google.Keystone.Daemon.Administration logEverything=0 logBufferSize=2048 alwaysPromptForUpdates=0 productIDToUpdate=(null) lastUIDisplayed=(null) lastCheck=2015-04-30 04:24:22 +0000 alwaysShowStatusItem=0 updateCheckTag=(null) printResults=NO userInitiated=NO>
    1/05/2015 10:39:44.654 am Timings[736]: AppTracking stopped due to sleep or shut down
    1/05/2015 10:42:46.000 am kernel[0]: ACPI: sleep states S3 S4 S5
    1/05/2015 10:42:49.323 am discoveryd[73]: Basic SleepProxy BSP Server Disabled. Metric = 3373
    1/05/2015 10:42:49.344 am discoveryd[73]: Basic SleepProxy Could not get the primary interface
    1/05/2015 10:42:49.353 am discoveryd[73]: Basic SleepProxy Sleep Proxy Server is not enabled
    1/05/2015 10:42:54.725 am discoveryd[73]: Basic SleepProxy Could not get the primary interface
    1/05/2015 3:38:01.187 pm GoogleSoftwareUpdateAgent[5941]: 2015-05-01 15:36:40.022 GoogleSoftwareUpdateAgent[5941/0xa0c2f1d4] [lvl=2] -[KSAgentApp setupLoggerOutput] Agent settings: <KSAgentSettings:0x319240 bundleID=com.google.Keystone.Agent lastCheck=2015-04-30 23:49:37 +0000 checkInterval=18000.000000 uiDisplayInterval=604800.000000 sleepInterval=1800.000000 jitterInterval=900 maxRunInterval=0.000000 isConsoleUser=1 ticketStorePath=/Users/phil/Library/Google/GoogleSoftwareUpdate/TicketStore/Key stone.ticketstore runMode=3 daemonUpdateEngineBrokerServiceName=com.google.Keystone.Daemon.UpdateEngine daemonAdministrationServiceName=com.google.Keystone.Daemon.Administration logEverything=0 logBufferSize=2048 alwaysPromptForUpdates=0 productIDToUpdate=(null) lastUIDisplayed=(null) lastCheck=2015-04-30 23:49:37 +0000 alwaysShowStatusItem=0 updateCheckTag=(null) printResults=NO userInitiated=NO>
    1/05/2015 4:59:19.731 pm Timings[3645]: AppTracking stopped due to sleep or shut down
    1/05/2015 5:03:39.164 pm coreaudiod[242]: 2015-05-01 05:03:39.163645 PM [AirPlay] Power: SystemWillSleep
    1/05/2015 5:03:55.473 pm discoveryd[73]: Basic BTMMServer Sleep offload failed. Start deregistering
    1/05/2015 5:03:58.000 pm kernel[0]: AirPort_Brcm43xx::powerChange: System Sleep
    1/05/2015 5:04:00.000 pm kernel[0]: hibernate image path: /var/vm/sleepimage
    1/05/2015 5:04:01.000 pm kernel[0]: Opened file /var/vm/sleepimage, size 8589934592, partition base 0x0, maxio 2000000 ssd 1
    2/05/2015 6:37:59.000 am kernel[0]: Previous sleep cause: -60
    2/05/2015 6:38:00.118 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: Reordering authw 0x7fc7a2c78d80(2000) (lock state: 3)
    2/05/2015 6:38:00.168 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: err 0x0
    2/05/2015 6:40:58.537 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: Deferring.
    2/05/2015 7:01:11.312 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: Deferring.
    2/05/2015 7:09:06.117 am GoogleSoftwareUpdateAgent[8440]: 2015-05-02 07:09:04.977 GoogleSoftwareUpdateAgent[8440/0xa0c2f1d4] [lvl=2] -[KSAgentApp setupLoggerOutput] Agent settings: <KSAgentSettings:0x545fe0 bundleID=com.google.Keystone.Agent lastCheck=2015-05-01 05:38:03 +0000 checkInterval=18000.000000 uiDisplayInterval=604800.000000 sleepInterval=1800.000000 jitterInterval=900 maxRunInterval=0.000000 isConsoleUser=1 ticketStorePath=/Users/phil/Library/Google/GoogleSoftwareUpdate/TicketStore/Key stone.ticketstore runMode=3 daemonUpdateEngineBrokerServiceName=com.google.Keystone.Daemon.UpdateEngine daemonAdministrationServiceName=com.google.Keystone.Daemon.Administration logEverything=0 logBufferSize=2048 alwaysPromptForUpdates=0 productIDToUpdate=(null) lastUIDisplayed=(null) lastCheck=2015-05-01 05:38:03 +0000 alwaysShowStatusItem=0 updateCheckTag=(null) printResults=NO userInitiated=NO>
    2/05/2015 7:19:11.035 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: Deferring.
    2/05/2015 7:35:18.701 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: Deferring.
    2/05/2015 7:37:35.421 am coreaudiod[242]: 2015-05-02 07:37:35.420950 AM [AirPlay] Power: SystemWillSleep
    2/05/2015 7:37:57.995 am discoveryd[73]: Basic BTMMServer Sleep offload failed. Start deregistering
    2/05/2015 7:38:01.000 am kernel[0]: AirPort_Brcm43xx::powerChange: System Sleep
    2/05/2015 7:38:03.000 am kernel[0]: hibernate image path: /var/vm/sleepimage
    2/05/2015 7:38:03.000 am kernel[0]: Opened file /var/vm/sleepimage, size 8589934592, partition base 0x0, maxio 2000000 ssd 1
    2/05/2015 7:38:28.000 am kernel[0]: sleep
    2/05/2015 7:38:33.000 am kernel[0]: Previous sleep cause: 5
    2/05/2015 7:38:33.393 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: NULL shield_window (lock state: 1)
    2/05/2015 7:38:56.292 am coreaudiod[242]: 2015-05-02 07:38:56.291574 AM [AirPlay] Power: SystemWillSleep
    2/05/2015 7:38:57.288 am discoveryd[73]: Basic BTMMServer Sleep offload failed. Start deregistering
    2/05/2015 7:39:00.000 am kernel[0]: AirPort_Brcm43xx::powerChange: System Sleep
    2/05/2015 7:39:02.000 am kernel[0]: hibernate image path: /var/vm/sleepimage
    2/05/2015 7:39:02.000 am kernel[0]: Opened file /var/vm/sleepimage, size 8589934592, partition base 0x0, maxio 2000000 ssd 1
    2/05/2015 8:16:54.000 am kernel[0]: Previous sleep cause: 5
    2/05/2015 8:16:54.588 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: Reordering authw 0x7fc7a2cc74b0(2000) (lock state: 3)
    2/05/2015 8:16:54.589 am WindowServer[147]: handle_will_sleep_auth_and_shield_windows: err 0x0
    MEMTEST
    Mac OS X 10.10.3 (14D136) running in multiuser mode
    Memory Page Size: 4096
    System has 8 Intel core(s) with SSE
    Requested memory: 10327MB (10829672448 bytes)
    Available memory: 10327MB (10829672448 bytes)
    Allocated memory: 10327MB (10829672448 bytes) at local address 0x0000000101000000
    Attempting memory lock... locked successfully
    Partitioning memory into 2 comparison buffers...
    Buffer A: 5163MB (5414836224 bytes) starts at local address 0x0000000101000000
    Buffer B: 5163MB (5414836224 bytes) starts at local address 0x0000000243bfd800
    Running 1 test sequence... (CTRL-C to quit)
    Test sequence 1 of 1:
    Running tests on full 10327MB region...
      Stuck Address       : ok             
      Linear PRN          : ok             
    Running comparison tests using 5163MB buffers...
      Random Value        : ok
      Compare XOR         : ok
      Compare SUB         : ok
      Compare MUL         : ok
      Compare DIV         : ok
      Compare OR          : ok
      Compare AND         : ok
      Sequential Increment: ok
      Solid Bits          : ok             
      Block Sequential    : ok                
      Checkerboard        : ok             
      Bit Spread          : ok               
      Bit Flip            : ok               
      Walking Ones        : ok               
      Walking Zeroes      : ok               
    All tests passed!  Execution time: 3076 seconds.

    Hi fatlinesofcode,
    First of all, check out Apples article on the issue: OS X Yosemite: If your Mac won’t go to or stay in sleep If you find these steps don't help, try a few of the following
    A common cause for the Mac not sleeping is your printer. If there are queued jobs waiting to be printed, but your printer is switched off, for some reason you Mac just wont like it and simply will not go to sleep. System Preferences > Print and Scan > Open Print Queue
    Do you have an Ethernet Cable connected? People have reported in the past that removing their Ethernet allowed their Mac to sleep. This goes for other things you may have connected directly to your Mac also.
    Try heading into your Mac Preferences > Sharing and deselecting 'Internet Sharing' as well as 'Printer Sharing'.
    Also deselect Wake For Network Access by heading to System Preferences > Energy Saver > Power Adapter > Wake For Network Access.
    Energy Saver > Schedule > Startup or Wake - Uncheck.
    Alternatively, set your system preferences to Never Sleep, and put into Sleep manually: System Preferences > Energy Saver > Computer Sleep > Never.
    Good luck!

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