#1
I've got this Highway One Stratocaster and I don't like it one bit.
The red nitro finish is ugly, it gets muddy with gain, I don't like jumbo frets and the rosewood neck is not so hot either, much like a MIM rosewood neck.

I'm a blues player and I've got the blues for some changes.
Should I get new pickups for $300 or a MIM Maple Sunburst Strat for $200
I'd like a vintage sound. Investing $1000 in a new guitar is not an option right now, I just finished college and I've got no job.
Fender American Standard Stratocaster/Seymour Duncan Hot Rails
Seagull Rustic
Fender Hot Rod Deluxe
MXR GT-OD
MXR Distortion III
MJM London Fuzz
EHX Big Muff
#2
If you hate the highway one so much why not sell it and get something you do like. They go for ~$600-$700 new right? depending on the condition you could probably get at least 400 for it. With that and your 300 you can get something new.

Why even consider replacing the pickups if you hate the guitar?
For Frodo!
Quote by jrcsgtpeppers
No because a world full of marbles silly man is just as real as a half empty glass of microwaved nesquik.