New phone and network questions!

It's coming to the end of my contract in the next few days, thank god, and I get to throw my crappy HTC Hero away (well, I have had it 18 months...) and so here starts the quest to find a new phone, but I have a few questions! Thanks to David (HotelUser), I'm definitely going to choose the HTC Desire or the HTC Desire HD (not sure which one yet though).

Here a few of my questions that I wish to ask :D I know there are some great technical gods out there so please feel free to help me out, +rep for serious replies of course.

1) I made the mistake of getting my contract direct with T-Mobile 18 months ago, and so they branded my HTC Hero and I had to rely on T-Mobile themselves to roll out updates (trust, it was the worst thing ever) so I have to ask, should I go 3rd party with a company like The Carphone Warehouse?
2) What other 3rd party companies do deals and are trusted companies?
3) If I go 3rd party with say The Carphone Warehouse, on the T-Mobile website it states that all Android phones get an unlimited internet booster (which I have now) - will I get this if I go with The Carphone Warehouse?
4) Is there any reason not to stay with T-Mobile?
5) Finally... Desire or Desire HD and why?

http://dl.dropbox.com/u/13410865/Scr...2002.14.13.png

I think the most serious questions are number 1 and 3 to be honest as they are what I need to know! I can't live without internet yet I don't want some branded heap of brick that I'll have to wait 3 months after HTC have rolled out the update themselves... (plus the tacky T-Mobile logo is dreadful, shame about Orange haha!)

Oh, and a big big note, this is not an upgrade! I will be starting a fresh contract due to family issues, the person who used to pay my contract is no longer willing and therefore, yeah...

Thanks to anyone who can answer! :)

Wait, I know you had to wait for updates through T-Mobile "Officially" but didn't you root and flash your Hero a number of times? :P

Quote:

Originally Posted by xxMATTGxx

Wait, I know you had to wait for updates through T-Mobile "Officially" but didn't you root and flash your Hero a number of times? :P

I don't really want to do that on my new device, I'd rather have the generic handset.

I purchased my phone from t-mobile I think..the best contract deal I found when buying my contract was with the tmobile shop who offered the unlimited Internet booster and unlimited texts

T-Mobile poorly supported the HTC Hero and I still can't update it because they screwed up (Basically to use the official ROM I have to flash it anyway). I'd go with the Desire HD, a magazine I've recently read just said it's better, can't argue with that logic, larger screen, better camera.