Great question. First off, if the only thing to do in Ham radio was to talk to a bunch of Phoenix repeater guys with starched shorts, I wouldn't be in the hobby. Yeah, the local 2m / 70 cm repeater stuff is about as boring as watching paint try, or grass growing. After getting my tech license I realized immediately that the local repeaters were cliquey, and too "stiff" and structured for my tastes. And really, a repeater is only supposed to be there for when you can't make a contact with simplex, and that brings up something much more interesting.
With simplex, you are forced to get more involved with the technical aspects of the hobby right off the bat. An HT with a rubber duck isn't going to get you far. You can get a good mobile setup going, and take a big step up from an HT, but you will find out quickly that a base installation can provide surprisingly good performance, and interesting challenges, especially with regard to installing and better yet, constructing antennas. I recommend getting a simple 2 meter radio to start with, and spending a little money on finding a way to get a decent antenna up as high as you can. All of the sudden the stiff formality (and boring conversations) heard on repeaters will be gone, and you can begin to talk to people, more as you would if just talking to someone on the street. Unlike what some will tell you, this isn't a bunch of "CB guys", who got into ham radio for the most part.
Here in Phoenix, a lot of guys listen / talk on local 2 meter simplex frequencies such as 146.52, 146.54, and 146.48. Don't let the informal environment and friendly personalities fool you, as some of these guys have been involved with ham radio for 40 - 50 years plus, and have a lot of knowledge to share. And learning from friendly folks in a relaxed environment is a lot more fun than the alternative. They also have something you rarely hear on repeaters, humor. It doesn't take long to catch the "HF bug", at which point you will find yourself looking for your first HF radio, and thinking about putting up a few "homebrew" wire antennas to get started. These local simplex guys will be happy to share their experiences, a few laughs, and plenty of friendly advice on equipment, antennas, etc. Many will give you the shirt off of their own back, and by this I mean they will stop by and help, share their time, help put an antenna up, lend an antenna analyzer, etc. The guys who regularly monitor 146.52 have lunch every week, and the group ranges from "Joe sixpack" types, to airline pilots and wealthy entrepreneurs. Everyone is friendly and helpful, always ready to help a new ham, always ready to stop a QSO and / or answer a break from a new ham on his first HT.
Once you enter the world of HF, you will be amazed at the possibilities. Talking around the world is really neat, and you can also just talk around the states too, if you like. On this last Sunday I talked to people in Scotland, South America, Africa, Australia, Canada, and many states here in the US.
Local repeater chit-chat, at least as it exists here in Phoenix, is the lowest common denominator in ham radio, so don't let that sometimes boring aspect of the hobby keep you from having fun as there is a lot more to amateur radio than talking on repeaters with an HT. I suspect that most who limit the hobby to that scope lose interest quickly. Remember, repeaters are supposed to be there for when simplex isn't possible with the person(s) that you need to contact. I don't mean to imply they don't have their place, or that there aren't some good guys on the repeaters, just that repeaters are just one small part of a large hobby. It just seems to me that some people get so wrapped up with repeaters that they miss out on some really cool things.
Enjoy your new hobby, and stop by 146.52 and throw out the call here and there. You might be pleasantly surprised to find friendly, helpful locals, who talk to each other, all over central Arizona, no repeater required.