So, I am planning on buying my second guitar amp and guitar (my first was a cheap squier strat and a basic line 6 spider 3 that I didn't like). Now, my plan was to get either a fender black highway one strat and maybe relic it, or more likely a fender classic player '60s MIM strat, with the custom show '69 pickups (i've heard they're have great tone). Any opinion on those would be great.

My bigger dilema however is the amp. Now, as for tone, I love John Mayer's tone the most, as well as people like Colin James (great player if you've never heard of him - http://ca.youtube.com/watch?v=M26AKmRwguk ). I really like a somewhat bluesy (not too bluesy tho) somewhat clean tone, that has a subtle break up like mayer's. I've been looking a lot at the fender tube amps under 1000, like the blues deluxe reissue, hot rod deluxe reissue, deluxe reverb reissue, blues jr, etc.

I'd love to keep my budget on the amp and guitar under 1000 each, less if possible, but i don't want to sacrifice quality. I'd rather spend a little more for something that i'll keep for a long time rather than cheaping out and needing to replace it soon.

Oh, and by the way, I have a great overdrive pedal (barber direct drive) and a great compressor pedal (barber tone press) so being able to really drive my amps isn't a great worry for me. As far as I know i'd love a clean tone that I can then use my direct drive on... is that a smart thing to do? or no? any advice would be great, i've only played for about 2 years, and i've had the same gear the whole time.

Thanks so much.
I'd say go for exactly what you're thinking about.. a fender strat.. try out a few to see which one you like best.. they are basically all similar though, so just pick the one that feels right

as for amp, i'd say get a fender tube amp, like a hot rod deluxe or something similar
My Guitars:
Gibson Les Paul Studio
Epiphone AJ
Ibanez Strat Copy

Orange Tiny Terror Head
Old beaten up Peavey cab
Marshall MG30DFX