Tonequest - the musical, or, barking up the wrong swamp ash tree

Playing my dead-sounding Highway One Strat at a theatre gig the last few days got me thinking about ways to try to resurrect this guitar, which I bought about two years ago for the rock shows I was doing at the time. I was trying to find a workable Strat for about a thousand bucks, and was enticed by the classic features of the Highway One, and the nitrocellulose finish, which is all the rage these days.

I've already changed out the pickups, dropping in a set of Rio Grandes in a SSH (single-coil, single-coil, humbucker) configuration and no dice.  The guitar still sounds like ca-ca. I'm not sure why I didn't hear it earlier, but this guitar just lacks presence, sweetness, lows, highs, mids...at the theatre gig I eventually just started using my much-better-sounding Mexican Telecaster, which I've had for over ten years.

My friend Rob Phillips changed up his late-80s Strat by switching out the body altogether, using a new body from Guitar Mill.  The body, with a custom sunburst, took months to show up but he's very happy with the guitar now.  Could a new body be the cure for my Strat's near-terminal suckiness? I can't help thinking that the guitar somehow enters a new stage of existence with a new body - every other part is subject to change and it's still THAT guitar.  But change the body and you change the guitar.  I'm not sure why this notion persists in my mind, but it does. But Leo designed his guitars to have easily replaceable parts, like a Ford Model T. It makes repairs much simpler and has also led to a culture of user modifications stretching at least as far back as Hendrix's white Strat with a Tele neck.

And what of options? Say I go with a swamp ash body ($185), humbucker rout for the bridge pickup (+$20), string ferrule installation (+$35) and Olympic White nitro finish (+$225).  Total is $510.00 plus shipping, duty, and currency exchange. And I still might hate the guitar.

Having played guitar now for almost 29 years, I've gotten extremely picky about my instruments, yet I find my tastes hard to articulate. My feelings about a guitar can take many months to settle, and I've bought and sold many, many electric guitars over the years trying to find the elusive tone and feel that I like. It's a bit of a sickness, and unfortunately for me modifications rarely do the trick.  There's something about the gestalt of the total guitar that has to be right, or I'll never be happy, it seems. Or maybe it's just a matter of research.