Buying used iphone and unlocking, do I need to buy Tmobile sim?

I'm wondering how this all works. (I use Tmobile as my service btw). If I'm buying a used iphone 3gs and want to activate it on Tmobile, what do I need to look out for? Does it matter what OS it is currently on? From articles I've read in the past it seemed there were certain OSes that didn't allow you to unlock the iphone. And I'm not sure what iphones can't be unlocked altogether. But, I'm wondering if I buy it, do I have to go purchase a sim card from Tmobile for it? Apparently this 3gs I'm looking at is OS 5.01, but I will have to unlock it or pay to have this unlocked in order to use it on my Tmobile service. Just wanted to make sure I follow the correct steps to get an iphone working on Tmobile.

" Seems like I'd be paying much more for an officially unlocked iphone. "
Becasue it is a legit iphone.  Hacked iphones get no support at all from Apple or this forum.  The warranty is void and many people have had their iphones rendered useless by hacking.
"I thought most services that offer hacked unlocking services have gotten the math down on how to do it safely and successfully. "
Not true at all.  This is a big risk.
" What is the danger from going this route? "
Hacked iphones get no support at all from Apple or this forum.  The warranty is void and many people have had their iphones rendered useless by hacking.
" Seems like most people have gone this route, no?"
No.
"Even if I buy an unlocked iphone, I'm guessing I will still have to spend extra money to buy a sim card for it, correct?"
You would have to ask the carrier.  I have never paid for a SIM card.

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