Certainly...there's an around the world trip coming up soon. Haven't seen anything in that price range...but there are things that can be done...I'd say they're more or less just for well off fanatics at this point as it will void your warranty. "Risk Problems?" I think it's more or less a matter of making it affordable with the desired capacity and without compromising the life of the batteries. We're all hoping/expecting something by 2010/11 Check the cost.
I've personally taken several two-four hour (one-way) family vacations with my wife and infant, and I thought it was perfect! The hatchback gives you a lot of storage space and you don't have to gas it up very much. There are some who argue that they don't like the seats, though. It's aftermarket through local shops and requires the car to be plugged in to an electrical outlet overnight. See California Cars Initiative for Plug-In Hybrids. In reality, if you take short trips, you may no longer need gas at all. The 150 MPG variety is a plug-in hybrid, as above, and would come at a several thousand dollar premium. If you can wait, it might not be a bad idea to wait till 2009/2010 until the third generation Prius arrives. Even if they don't have the plug-in models available yet, there will probably be some efficiency improvement or other neat perks.
Loaded up me, my wife and camping gear for two weeks. The Prius was filled to the brim. Went from Chicago to Colorado and circled the state over 2 weeks. No problems. High mountain passes - no problem other than dropping to 45 mph on the steepest parts at high elevation. The motor gets a little noisy and the battery drains to one bar, but not to worry. Roomy enough up front, and neither me nor my wife are small. I better rephrase that. We are both around 5'-11". Although the seats are not the most comfortable, they're "doable" for a cross country trip. I drove straight through. We left Chicago around 6:00 Friday night and were in Golden for the Coors tour Saturday morning.
We have gone on several climbing trips, where we had our Prius loaded with four adults and climbing and camping gear, sometimes going for 11 hours in a single day. The car is full, but it works just fine. My advice: Forget worrying about what's coming out next year and get one now. You will wait forever if you try to catch up with technology. Tom