I feel special...but no wonder it's so lonely here. Thanks Scott for keeping the riff-raff out!!
I don't think one can ever really say one truck is better than another, they all have their advantages and disadvantages. In the end, it's really about what you want to drive and getting it prepared to go where you want to take it. I've never owned a rover but really love and respect them (g-wagons and lc's as well). I'd suggest hooking up with some owners and riding shotgun on some wheeling trips to see first hand what you like/dislike about each truck. Try other trucks as well...don't think only a hummer or rover will do...and don't just get one over the other because someone says so, get what's right for you, and what you can afford. Wheeling is an expensive hobby -- it's easy (and addicting) to go crazy with accessories and vehicle modifications not to mention the increased maintenance. You;ll learn a lot from talking to owners.
I've had my '97 td hummer for 6 years and it still makes me smile whenever I drive it. I bought it primarily to be my trail truck, so I have another car that I use as a daily driver. Not to say it doesn't make a fun/reliable daily driver (I know many who use it as such) but I often have to park in garages and/or use valet and I don't like handing my truck over to strangers. People have the impression that there are so many but in my experience most can't tell an h1 from and h2 from an h3. The h1 has nothing in common with the latter two. GM bought the name and borrowed the "styling" from AM-General, who sold less than 12,000 civilian hummers between 1992 and 2006. It is estimated that there are maybe 8000 left in the US.
I really don't think it's as unreliable as most here will say, but it's certainly no Toyota! It's easy to work on and I haven't found parts from AM-General to be that expensive. It will go through a lot of idlers, pitmans and balljoints if used a lot off road. As long as you follow the maintenance schedule it will last forever.
The only reliability issues I've had are with all the aftermarket stuff I've added to the truck and the computer on the GM 6.5 engine. My mechanic is one of the most knowledgeable in the world about these trucks and tells me that 95% of the h1's is towed/flat-bedded into the dealer is a computer related issue. If I was to do it all over again, I'd get an earlier model with a na diesel -- less complicated, more reliable.
What will kill your bank account quick is a few visits to a Hummer dealer -- and it's hard to find them that can actually work on these trucks. Most dealers say they can work on them, but really don't know a ton about these trucks. GM started screwing that up almost immediately after buying the hummer name from AM-General around 2000, so you won't see many h1 guys sad about GM tanking. AM-General is totally separate and will be around making stuff a long time. As long as humvees are in use there will be plenty of parts to be had and people to work on them when you can't.
Driving on road is much more comfy than other equally capable trucks I've been in, but louder. It's no caddie, it's closer to a tractor -- so I am baffled by most of the folks who buy these trucks because of the impression they are so luxurious and roomie. These trucks hate chrome and will stop working until you remove it.
It's offroad capabilities are amazing, however one really needs to learn how to drive it properly (the half-shafts can be easy to break if you don't know what you are doing). H1's are on portals so there is a lot of ground clearance -- 17" with stock 37" tires. It can use up to 38.5" tires...any bigger and you'll probably want a body lift so there will be no rubbing. With a 2" body lift you can fit up to 42" tires (again, knowing how to drive it will keep it from becoming a half-shaft breaking machine).
It's low and wide, so it's very stable on and off the road. I rarely find the width limiting on trails, but admittedly I mainly wheel in the Big Bear, Arrowhead, and desert areas amd haven't spent too much time in forrested areas. There's a rear steer kit out that makes these things turn like a smart car that I am really interested in. It will eliminate those 20 point turns on narrow switchbacks! If you are ok with brush rake or desert pinstriping then you'll be fine.
Like I said, talk to owners, ride in and drive all the different kinds of trucks you can get your hands on to give yourself a fairly good idea what will work for you. You are near Chicago so you are not far from the AM-General factory, it's in South Bend -- go take a tour, I hear they are cool. Sorry for blabbing so much.
here's a fun promo video from the mid 90's:
http://www.youtube.com/watch?v=NiIot7CDRg8&feature=related