Pardon me, but I get this impression that the real reason you never jailbroke your device is because you never intended to keep it. It didn't make sense to me that somebody who has rooted every Android phone they've used, would be hesitant to jailbreak the iPhone. The only complaint that you had that couldn't be fixed with a jailbreak was the size of the screen. You wouldn't want to jailbreak a phone you intend to return.
I took interest in your posts because I am very interested in the HTC Thunderbolt and the nearest sized phone was the Droid X, your old phone. Like the commerical ad says, "It's not your dream phone. It's the one after that." Well, my dream phone is an iPhone. And the Thunderbolt does come after the iPhone, with 4G speeds!
Altthough, I can get into a Droid X for a whole lot cheaper than a TB. So, I have been spending time checking out both the Droid X and iPhone. The noticable difference between the two is the size of the screen and the fact that you can watch TV shows from network web sites in your stock browser, which you can't do on an iPhone.
With a HTC Thunderbolt, I can replace cable and high speed internet with the 4G speeds. I have LTE in my area. Figuring that Verizon has already said they will be going to tiered data plan pricing at some point in 2011, would I still be intereted in a 4G device if I kept my cable and high speed internet? With the Thunderbolt running at least $265 out the door, with NE2 and minimum tax applied, versus a Droid X for $153 out the door, likewise.. Is 4G worth the extra $112? (In my area, sales tax is 9.5% minimum, and Verizon will add the tax based on the retail price of the phone. ) Decisions, decisions...