There are only two ways I recommend Android - use a Google-branded phone that Google will provide complete OS support for, or go it alone with OS updates from a 3rd party.

For non-geeks the first option is the only viable one, IMHO.

You've obviously settled on the same conclusion.

Could you point me in the right direction for 3rd party?

I guess zdw is referring to Cyanogenmod. There might be others, I don't know.

On my (contractless) Galaxy S2 - OTA updates happen never, I have to connect to a Windows box for updates.

Do you know how OTA updates are pushed out for the non-Google Android phones that are bought without a contract?