I'm a new ham and plan on doing the same thing. I'm going to start with a Vertical with moderate gain, just enough to reach some of the more distant repeaters. There is only one local repeater. I'm in a rural area so interfearence should be far less than urban areas.
I also put an antenna on my vehical to help get the signal out while driving.
Down the road, I'll upgrade to a good higher power base UHF/VHF radio with SSB and a higher power mobile for my truck.
Money is tight so I'm going to make the best use of my handheld until I can upgrade my station. Of course the handheld will always be a part of my equipment.
I plan on staying with the UHF/VHF bands for a while and when I find a good deal on a used HF transcever, I'll get the 20 to 160 bands. I very much want to get a higher power 6 meter rig. It is a band I want to work, especialy with the sun spot cycle where it is now.
My best to you and experiment, that's what radio is about, John K