I usually recommend noobies buy equipment incrementally since you can spend a lot of money fast if you get radios +antennas for handheld, car and home. A good plan is to start with a good handheld. In the car, you can use a mag mount antenna with an adapter for the handheld to improve your range until you decide on a mobile rig, also good for second vehicles. In WW, the handheld should serve well at home with the local repeaters but simplex across town will be problematic, again, you can add an outside antenna with an adapter.
An additional consideration is band you plan to use. Down the hill 2m and 440 are the most common. In WW, 2m and 220 have been the most popular/active; however, WCG is in the process of acquiring its own repeaters and repeater pairs. The 440 machine is up, the 2m pair has been approved so equipment will be coming, and hopefully the 220 pair will be approved in the near future.
That being said, a good handheld that suits all needs in one package is the Kenwood tri-band TH-F6A. Dual bands are usually 2m/440. Diamond makes great antennas and are my favorite, Toolman can help you out with a tribander, we just put one on my truck.
Mobile rig is a harder ticket. There are currently no tri-band radios in the 2m/220/440 flavor in production. Toolman has, and I was able to get used, the Kenwood TM-741 'family', they were offered with two bands built in and an option for another module. Very hard to get now and they haven't lost value. I'll leave discussion on drawbacks of these units to Toolman as we've learned they can be sensitive to heat and bad swr, especially if you chat a lot, however, with a added fan and a good antenna, there should be no problem. Otoh, since it's a discontinued item, parts are becoming scarce as well. Alternatively, a standard mobile 2m/440 rig would perform equally well in the car or in your house.
