New ham here as well, coming up on my 1 year anniversary. Decided to go with handheld for the moment, but looking at getting a super serial setup for my 109 soon.
I went with an Icom ID-51...used. Well received and highly regarded piece of equipment. Everyone says you should have a handheld, so why not get a good one? What I like about it is how portable it is. I can easily switch between cars and even recently had it in a rental. Coupled with a cheapo mag mount antenna, it works very well. On my 109, I mag mount it to the ARB bull bar.
Impressions: I can hit repeaters within 20 miles, assuming I'm not in a hole. That is pretty good for only 5 watts! Its nice being able to have a ham radio...and just walk around with it. I have three active repeaters near my house, ranging from 2 to 15 miles away. If I'm on my back deck, I can hit all of them no problem. If I'm in the house, I can hit the 2 and 6 mile one easily. Sometimes I can hit the 15 miler one...but it depends on atmospheric conditions.
Often I'll take it on road trips and see what repeaters I can hit. There are a lot of "dead" repeaters out there. Kinda interesting.
But yeah. I would say start with a good hand held...that you'll want anyway and a mag mount. Go from there and see what you want.
Also what do you want to get out of ham radio? Initially, I wanted it for off road communications. A simple Baofeng works just fine for that, can call on simplex for a few miles easily. If you are talking to others over 2m...at a large distance, then higher wattage and better antennas start to make sense. I'm wanting to get into APRS, so now I'm looking at radios with integrated GPS and APRS, etc.
I never really had goo luck with the Baofeng radios. I tried the BF-9...whatever. It sucked. I could be LOOKING AT THE REPEATER and get no joy. I did play with a UV-5r for a while, it seemed a bit better. But either way, the Icom blew both of them out of the water in terms of performance. I could have a Baofeng with a nice antenna, and the Icom with the stock antenna would out-perform it.
One thing, ALWAYS get the programming cable and software. For whatever you get. Otherwise you'll be stuck fiddling with complex menus and other pains that just aren't necessary.
So yeah. I would cruise eham.net for a good used handheld. That way you can save a few bucks, but get quality equipment. I'm looking for a nice mobile radio, and I'm definitely going used. The one I'm looking at, probably 1/3 the price of a comparable new radio. My ID-51 was less than half the price of new, and only a few years old.