After resisting for as long as possible the urge has taken hold. My employer pays for my cell phone/service but they've taken a hardline against iPhones. That being said they use AT&T and I think I'd like to try and unlock and jailbreak an original iPhone (with my current SIM of course).

Since ebay seems to be the only place I can purchase a 2G iPhone (without a contract). I find myself very untrusting of many of the auctions I'm seeing - Not to mention I'm weary of basically paying full price for a used phone. For the sake of avoiding an obvious scam (and being an iPhone newb), is there a question that I can ask the sellers in order to establish that the listings are real?

Or am I just crazy for wanting to try?

Best way I know of is to take a look at feedback. If the seller has 100 feedbacks and is 98% or better positive, it is a good bet that he is reputable.

If payament is made through PayPal and the auction turns out to be fraudulent, you will be protected for the amount of the purchase.

tanstaafl.

I also check how long they've been registered.
Under a year, be very careful. I've also seen accounts with zero activity for 2 years and then a few months of rapid selling.
Also note what else they've sold and the value.

I only tend to bother with this kind of digging if the item is easily stolen or expensive.

Pay with your credit card via PayPal and you're totally protected regardless of the outcome. That's two levels of protection, because you can always go to your credit card company if PayPal doesn't resolve the situation for you. With an online transaction, you can pretty much have anything reversed since there's no proof of signature. Which is itself a source of scams from the other end, but that's another topic.

Purchased through a (somewhat) local ebay store... Their feedback wasn't stellar but it was in the range of what I'd consider acceptable.

Should be here tomorrow. I'll let you know how it turns out.

Received my iPhone today!

Couldn't be happier with the purchase!

Great condition and working perfectly.

I was thinking about selling my 2G iPhone after I had to replace my 3G yet again ($300) when the screen cracked in many places. But now I'm so pissed off at the Apple customer experience (the silly little glass houses filled with annoying people - they call them "Apple Stores") that I'm using the 2G to help out with the iPhoneLinux project. Mine's happily booting Linux now Such damned nice hardware, crippled through locked down software, and a paranoid turtleneck who won't let people do what they want with it.