Why would you want two nicely equipped "GMC Yukon or Chevy Tahoes for the same price."? Sound like two pieces of junk. But you COULD buy a nice capable SUV and also a nice capable sedan or roadster, and I'll agree that two is better than one.
I actually looked into buying an H1. The things that stopped me were:
1) Lack of reliability data. I have one car with 150k miles on it and a Jeep with 60k miles on it. I am very confident in both of those and know the history of their models and likely problems. In my brief Hummer research, I found VERY few that had high miliage, and VERY little data, anectdotal or otherwise to suggest what might go wrong or counted for common problems. There was also next to zero data for repair costs, parts cost, etc.
2) Insurance - I didn't go so far as to try to get a quote, but reading owner's comments and things like that, I got the impression it was absurd
3) Speed - the H1s are pretty damn slow. I'm not even sure if they'll do 70, and 0-60 is in something like 20 seconds? That actually makes them a little dangerous for driving around here, especially on the interstate
4) Just too big - they won't do well on the interstate, but they also won't do well around town, because they're a little too WIDE to deal with narrow twisty roads, or even parking spots.
I do think they look fantastic, and purchase price wasn't even so bad - I found a couple that looked good in the 25-35k range - but it was just too impractical and too "unknown" to seem worth buying. Even though the initial cost wasn't all that outrageous, it seemed like the ongoing expenses could REALLY add up.