Re: Extremely New. Need Advice
I'd suggest a decent mountain bike with good V-brakes and normal size frame tubing.
Bolt a china two-stroke on it and buy a larger rear sprocket for the hills. Easily under $200 for the kit and sprocket.
Spend the rest of your budget on a HD chain and a quality brand bike with a large layout for your needs. Trek, Diamondback, Specialized, GT, Gary Fisher, Schwinn, etc. are all available for good prices used.
If more is better, then too much is just enough.
If you can't afford it, build it yourself.