As a former Squid myself (FC2) Let me be the first to welcome you.

Typically you would start with a high wing trainer because they're a lot more forgiving and can take a beating. I would make one suggestion for you to look at. Hangar 9 makes a P-51 trainer plane which looks like a P-51 but fly's like a trainer and is fairly durable. A friend of mine has one and I've flown it several times. In my opinion it does fly just like a trainer. It is a Ready To Fly (RTF) airplane meaning it has everything you need except the fuel & field accessories you'll need to start it.
http://www.horizonhobby.com/Products...ProdId=HAN2825
It is a little higher than your budget, but it is a warbird.

If you're looking for something a little cheaper just to get a plane in the air I'd recommend the Tower trainer http://www2.towerhobbies.com/cgi-bin...I=LXCXF4**&P=0 It fly's very well and is one of the typical high wing trainers I described earlier.

I can't really help on the heli front. I have never flown one.

**Edit**
Also, I would strongly recommend finding a local club to join because your plane won't last very long if you try to go it on your own. You may even check around with your local clubs to see if they have club trainers. My club has several trainer planes for new people such as yourself to come out and learn how to fly on so you can learn to fly while your saving up for that PTS Mustang.