Ok, my problem.

I was going to get a Highway One strat with the thought if I bought good equipment now, I wouldn't have to upgrade later.

However, 750 is a bit much, I must admit. I have, personally, a budget of around 500-600.

Now I'm thinking just to get a MIM, or maybe the Deluxe Player's strat. Or they have a beautiful Showmaster in the shop.

No worries about the amp, got it covered.

Help me out here guys. Should I continue with the Highway One, or go with the Deluxe Player's or the Showmaster?
Deluxe Player's the one with the button that can give you all of the pickup combinations, right? If it is, get that.
"Notes are expensive. . .use them wisely"-B.B. King

"It's been very important throughout my career that I've met all the guys I've copied, because at each stage they've said, 'Don't play like me, play like you."-Eric Clapton
Classic/blues type rock, and that clean grunge, ala Pearl Jam. Know what I mean?
i would take the Deluxe Player's mate it just looks so stunning i dont know how you can not buy one
Play them all and find the one you like best. A difference of a couple hundred dollars doesn't mean that one guitar is vastly superior to any other. I personally don't like the 12" radius on the deluxe player strat, which I was going to get, so I got a MIM standard instead. I haven't tried the newest H1's but the older ones I played didn't seem to be of any higher quality than any of the MIM's I've played.