The first question I would ask myself is, "exactly what do I want the radio to do for me?" There is a variety of frequencies to Hams, and the different frequencies offer different ranges of communications. If you need short-range comms, you will need a 2 meter rig. Longer-range comms are usually done with an HF (high frequency) rig.
Do you want to operate mobile from a vehicle or from your home/base location? Vehicle operation will require your rig to operate from 12 volts DC. The same radio at home will need a 12 volt DC power supply of some type.
Do you want to operate while hiking? The best type of rig for this would be a HH (handheld). These rigs, however, are limited in their range.
And in the final analysis, it's antenna, antenna, antenna. The type of antenna you use and how it is installed will make or break your comms.
I doubt that this post really appears to answer your questions. There are a number of manufacturers for Amateur equipment, and many of the radios have similar features. My best advice would be to decide what you need. After a while here with this bunch of folks, you'll get enough info to make a good decision.
Just keep that money cool and don't let it burn your pocket!!