I have a 50s RW and a HWY1 and I really like both. My RW is without a doubt more comfortable playing for me. It has a really decent tone. A bit hotter than vintage tone. I use it for playing blues and raw rock. I use my HWY1 for modern hard rock/metal. I have the HSS version. It handles the heavier/faster stuff due to it's electronics and flatter fretboard. The large frets took some getting used to. I really like both and they each have their purpose.

If needed I'd let the HWY1 go before the RW.

The RWs are a little too pricey imo and I wouldn't buy the whole "HWY1s are AMERICAN made". I think that's probably BS. Assembled in America maybe.

You have to play as many of each model as you can and make a choice based on playability and your musical preference. ALL guitars need set-up at some point. A reputable shop will set a guitar up if that's what it takes.

There are a million horror stories on this forum about the build quality of both Fender's guitars and amps. Some claim to have never played a decent RW or this, that and the other. There are claims that all the modern Fender amps are junk. Whatever. In the 25 plus years I've been playing, I've never purchased a bad guitar or amp. That goes for my low dollar to high dollar equipment. That either makes me the luckiest man in the world or the exception.

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Fender 50th Anniversary Strat
Fender Road Worn '50s Strat
Fender Highway One (HSS) Strat (D standard tuning)
Fender '72 Tele Deluxe
Fender Hot Rod DeVille 212

Well, I definatly prefer the sound of the sixties one. No competition there for me.

However, I don't like the road worn ones. They look super cool, but fake. If I wanted a road worn one, I would want to buy a new one and let it get into that state - to give it character.

I realise i haven't really concluded here.... I say 60's. The sound is amazing and it feels better to play in my opinion

I have a HW 1 that I really, REALLY enjoy playing. It sounds awesome and just has a killer feel to it. The jumbo frets didn't take long for me to get used to and I don't mind switching back to another strat I own with mediums. I have played a few RWs and they were nice enough, but they just didn't move me the same way. Might be the tighter radius or just the fact that they are pseudo-warn... In any event, HW-1 gets my vote.