Can't sync any apps to iPod Touch? (ver. 2.1.1)

Hi there, can any one tell me why can't I sync apps to my iPod Touch 2 Gen? My firmware ver. is 2.1.1. Thanks

I'm in a similar boat.
I should have 4 apps installed on my iPod Touch 1st generation (version 2.1), although only 3 appear right now -- I'll get to that in a moment.
My real problem is that the apps do not show up in iTunes. They are not listed in the Applications section nor do they show up on the Applications tab when the iPod is selected. When I connect, the title window indicates that Remote, Koi Pond, and Google Earth are being backed up, but they do not appear anywhere else in iTunes. Music I purchase on the iPod does get transferred to iTunes and appears in the library and in the "Purchased on iPod" list, so the basics seem to be working.
The reason one app is missing has to do with app updates. I obtained the Simplify Media (SM) app while it was free, and there were several updates after that. Trying to download the updates either failed or caused SM to appear a second time. The only solution seemed to be to delete it and then "buy" and download the updated version. That worked acceptably well until somewhere along the line the apps stopped appearing in iTunes. Now SM is no longer free, so my previous purchase seems to have been lost
Does anyone have an idea how to get the apps to become visible in iTunes again?
If I "repurchase" Simplify Media, will the app store realize I previously "purchased" it and let me simply download it again at no additional cost?

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http://osxdaily.com/2010/11/24/fix-for-no-content-on-iphone-ipod-after-ios-4-2-1 -update/
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Can't sync any apps to iPod Touch? (ver. 2.1.1)

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