All good info...WoW
If you have a laptop and a fast internet connection at home or while traveling, there is another option as well.
The ECHOLINK software will turn any laptop or PC into a radio. All one needs is a verifiable call sign, a laptop or PC, a headset/microphone, this program.
http://www.echolink.org/
This will get you on the radio - even before you buy your first one! ECHOLINK will let you surf repeaters
all over the world - for free!
When you are ready to pick out a 2m/440 radio, as mentioned before - any major brand is fine. You will need to decide what features suit your needs. APRS is useful and there are a few chasers who find it so. Saving a few bucks here isn't always the thing to do.
Kenwoods - IMO - haver nicer user features. Back lit buttons are standard, ECHOLINK ready (some are), APRS available, and larger LCD screens. Make nice repeater system for that reason - too. Nice! But any dual-band radio will suffice.
Like Joe Dorn, I have a Yaesu FT-8800R. It has a built in scanner for police/fire/emergency, a VERY useful thing to have. But all of these brands have one common need that isn't supplied in the box with the radio - a programming cable and software. They will hit you up for another $50 for that package before the radio you picked out is really complete. Keep your wallet handy!
If you want to save a stitch in time and have the extra $$$, a Icom IC-706MkII will cover 2m/440, and all of the HF bands and 6m as well. If I had the extra $$$ before I bought my Yaesu FT-8800R, I would have bought that one instead. A very complete and uncomplicated radio that delivers all of the goods.
I cannot stress enough how important a good antenna is to your system. This is simply one area where saving a few dollars isn't the thing to do. Get the best one that you can, and your purchase - whatever radio you choose - will be more capable when out in the boonies. Simply put, buy the best antenna and budget your radio choice accordingly.
Welcome to the useful, interesting, and expensive world of Ham radio!