Oh my, you've asked a broad question!
Which kind of radio and why (which you seem to be asking) is like which kind of firearm and why.
But let me take a stab at it.
The palace to start is with a uhf/vhf HT, for a verity of reasons
1) It is comparatively inexpensive
2) It is comparatively easy to operate and very portable
3) It is a required item for tactical communications (very important)
4) It works in the most commonly used segment of the HAM bands in North America.
You really, really, really want your HT to cover both the 70cm and 2 meter bands. Now-a-days that comes in a single radio as a matter of course (not as expensive as it used to be). Or you can start out with two radios, one on each band.
You also want to have an HT that is rugged and weather resistant.
once you have that under your belt, you'll want more power/range (although you'll be surprised what you can do with an HT using the right antenna and placement).
That's when you step up to the mobile VHF/UHF unit. They commonly run at 50 watts output (or about 10 times what your HT does) and is easier to operate when you are in you ZPAW crew wagon. Once again, great for mid-range tactical comms and uses the most common frequencies.
After that comes HF, mostly as a base station unit for tactical AND strategic communications (hey Ethyl! There are survivors over in that state, 1,200 miles away!)
HF can be used to good affect for mobile tactical communications, but it takes a lot of work to set it up.
To give you an idea, using a 2 meter mobile, FM voice mode at 50 watts simplex (no repeaters), you will get (if everything is good) LOS (line of sight) to the horizon, from the height of your antenna (50 miles?). Using HF SSB at about 80 meters and a mobile NVIS (Near Vertical Incidence Skywayve) antenna, you will have solid coverage out to 4 or 5 hundred miles easy and skip zone after that.
So the answer is what kind of communications do you want, then that tells you what kind of radio you need.
As far as modes, the minimum is voice mode in FM for VHF/UHF and SSB for HF. The digital modes are great and there are a lot of cool things you can do with them, but in the PAW, Voice is King.
Leethal wrote:Doctor Jest wrote a great post about what types of gear is out there, but I'd love to hear some more details from those of you who are experienced. Specific equipment recommendations are welcome, but I'm trying to get an idea of the general direction you have taken with your equipment purchases and the all-important "why."
What features in your radios are your "must haves", "nice to haves", and "do not want"... and why?
Specific features of interest: Crossband Repeat, Digital Voice and/or data, APRS, Multi-band, Wideband RX/FM broadcast/AM broadcast, etc.
Given your experience, and assuming a HAM has at least a general license, what would be your recommended "order of acquisition" of equipment, and why. For example, Mobile VHF/UHF -> Base HF -> Handheld VHF/UHF -> Mobile HF -> etc.
If you have multiple radio types (VHF/UHF/HF, Base/Mobile/HH, etc), which is your favorite and why?
I know this'd be a lot of work, but I'd love to hear y'all chime in. I've tried to search for this on QRZ.com, but it's the biggest flamefest this side of arfcom general chat, and eham.net hasn't "done it" for me.