If I had $300 I'd try and score a G+L tribute off ebay.
Still, if you have a strat and a radio shack amp, I'd think the amp would be the thing to be replaced. You could get a Vox Pathfinder amp for under $100 and have a nice little amp.
Are you playing with other people yet? What sort of stuff do you play?
Don't fret about "falling behind" or looking uncool. Just keep practicing!
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