I'll correct my earlier post... I meant to say CAN rather than CAN'T in my sentence saying "You can't (CAN) get a high end Squire for that much ($250). You might even be able to get a Mexican Fender on EBay for that much"
Indeed.. you can get the best Squire has to offer for around 250 USD.
As far as amps are concerned. It's the last in the tone chain.
Pickups>Effects>Amp
I would work your way down that chain. Start with a guitar that gives you the tone you want... Then get effects that compliment and accent the tone you want... THEN get an amp that brings out all the color and characteristics of the tone you want. That's my advice anyhow...