ITunes w/ iPod touch 2d gen & iPhone 4S... ?

I learned that my iPod touch 2d gen 32gb will no longer be supported, during the same week that I learned I am eligible for a phone upgrade. After doing a bunch of research, (I can't believe I'm saying this) I'm thinking iPhone 4S 16gb. It would be my first iPhone.
Is this utterly stupid?
In the time I've owned my iPod touch, iTunes has wiped it so often, and eaten ITSELF so many times, that since winter 2009 I have developed some anxiety about sync'ing, and about using iTunes generally. Like, I cringe everytime I touch the connector, and my palms hurt when I plug it into the device. I have kept the software up to date. Perhaps this is the problem?
Does anyone out there use an old iPod touch and a new iPhone (4S) with the same instance of iTunes and the same Apple account? Does it work? Is it a nightmare?
I know that these software/hardware relationships are crazy complicated, but I can't shake the feeling that Apple either doesn't take our data seriously, or needs to come up with a 'thief-identification' algorithm that knows the difference between a messed-up software update and a copyright/license infringer/violator.
What I'm reading on the boards and hearing in meatspace about the iPhone and sync'ing with iTunes, is the opposite of reassuring.

My question is about version compatibility. The question again, minus the chattiness:
My iPod touch = 2nd gen, meaning, it's a 2008 device, meaning: no iOS 5. Will it still sync with the newest version of iTunes?
I might be getting the iPhone 4S. A 2011 device. Which runs on iOS5 and needs the newest version of iTunes.
Is there a way I'll be able to sync these two chunks of hardware, of radically disparate ages/generations with the same instance of iTunes?

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    شركة نقل اثاث بالرياض شركة رش مبيدات بالرياض شركة رش مبيدات بالرياض شركة مكافحة حشرات بالرياض كشف تسربات المياه كشف تسربات المياه كشف تسربات المياه شركة تنظيف خزانات بالمدينة المنورة نقل اثاث بالدمام شركة تنظيف منازل بالمدينة المنورة شركة كشف تسربات بالمدينة المنورة غسيل وتنظيف خزانات بالمدينة المنورة شركة تنظيف خزانات بالرياض شركة تنظيف فلل بالرياض نقل عفش شركة تنظيف بالرياض شركة تنظيف بالرياض شركة نقل اثاث بالرياض  شركة نقل اثاث بالرياض شركة تنظيف فلل بالرياض شركة تنظيف منازل بالرياض شركة تنظيف منازل بالرياض شركة تنظيف منازل بالرياض شركة تنظيف منازل بالرياض شركة تنظيف خزانات بالرياض نقل اثاث في الرياض شركة مكافحة حشرات بالرياض شركة تنظيف  شركة نظافة بالرياض شركة نظافة بالرياض شركة نظافة بالرياض شركة نظافة بالرياض شركة نقل اثاث شركة تنظيف مجالس بالرياض افضل شركة تنظيف بالرياض افضل شركة تنظيف بالرياض شركة تنظيف موكيت بالرياض شركة رش مبيدات بالرياض شركة رش مبيدات بالرياض شركة تنظيف شقق بالرياض شركة عزل خزانات بالرياض شركة مكافحة حشرات شركة تخزين اثاث شركة نقل اثاث الرياض شركة عزل خزانات بالرياض شركة مكافحة حشرات بالرياض شركة تخزين اثاث شركة نقل اثاث الرياض 
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