Alright so right now I'm playing on an extremely cheap Dean Vendetta xm and some peavey travel amp. I eventually want to upgrade both but I'm not that serious about my playing, so I was wondering which I should upgrade first? Budget is about $250 for a new guitar or amp - I could maybe stretch that to $300.

(There are no guitar shops in my town and I've been to a few pawn shops in the area but didn't see anything I liked) So I'll probably be purchasing off of ZZounds.com.

So ISO suggestions on guitars or amps in the $250-$300 range. Thanks.

a 300 dollar guitar is a waste of money if you wanna upgrade, because your gonna have to upgrade again
Save a few hundred more dollars and geta a nice guitar.
You could prolly find a decent combo amp for 300 used

you can try to find a used Jet City JCA20C or Blackheart Handsome Devil on craigslist for about $300. I'm assuming you're into heavier sounds. Around here, Blues Juniors go for $300 on CL all the time, but that amp probably won't suit your style as well as the other two.

Imo if you're not too serious about your playing you should get a line 6 spider series amp. They simulate the sounds of different types of amps from clean to high gain. They're extremely versatile and good for beginners.

Worst advice yet. Those amps all sound like complete shit dude.

Obviously for someone that knows what a good amp sounds like and what kind of a tone you're capable of achieving with an authentic amp. But for someone that isn't a tone freak they aren't bad at all. He said he wasn't serious about his playing and that amp is exactly in his price range and will do exactly what HE needs it to do.

im agree wiht you Ling6= garbage
but this man is on a budget
You pay for what you get

I cant say this argument would be any better.