I keep hearing that 2.2 wont be an OTA, so if for whatever reason you cant get OTAs, then it wouldnt matter.
2.2 WILL put AT&T/Samsung Bloatware back on your phone. It is just "updated" versions of the same crap, but it is there. If you use a custom ROM, like Cog. it is all been hidden and disabled. I believe TiBu will be able to freeze the 2.2 crap too. If you root, you will probably have to re-root for 2.2.. no biggie. But I would un-root before you update just to be safe, you'll have to redo it anyway.
When I updated to jh7 , I did it OTA with root. It worked fine and I didnt even lose root. Is yours failing to connect, or is it just not finding it or what? Not that you are missing much, but have you tried clearing the data cache?