What you need is versatility... keeping it fresh will hopefully keep inspiring you to play. I'd suggest looking at Line 6 spider amps - they're solid state but have tons of effects built in, and are easy to setup and use.

Guitars? Squires are very very good for the money, and I've still got one. Ibanez are always my personal recommendation. As the guys are saying, think about splitting your money down the middle.... then play every $500 guitar in the store and see what you like the best... you'll know what's right when it's in your hands.