Sounds like your in the same boat I am. Read this post:

http://www.nexusoneforum.net/forum/n...eady-dead.html

for 1 possible answer to OTA updates and this:

7 out of 10 Android Phones Never Ran Up-to-Date Versions of OS

to see what was done in the last year regarding OTA updates. I would hate to get a 2yr contract on a phone and never get a freaking update. Choose wisely.