this might be helpful in that endeavor. The ARRL's official book is nice, but I'm enjoying reading this (very to-the-point vs. ARRL's conversational tone; Take your pick.)
If you're looking for your first HT, the Baofengs are about the minimum I would suggest. The DMR you can get is also super neat.
I got a Baofeng and then cannibalized a mic/speaker handset thing so I could do APRS and SSTV. So far, it's been an exercise in a little patience but I got it working eventually!
If you've got a bao~~tato~~feng already, get a nice antenna for it. Diamond's stubs and Comet whips are pretty nice.
If you want to peek into Software Defined radio, get an RTL-SDR. They make nice first-time UHF/VHF receivers. NooElec probably has one of the better ones.