So I finally put a new HSS set into my SSS Cutlass. Figured I'd check in and share my thoughts in case anybody else is following this.
The mod is fairly straight forward if you can operate a soldering iron. You'll need to desolder 3 wires to get the old pick guard out. And solder 3 wires in to get the new pick guard working.
There are two wires (green and white) going from the old pick guard to the output jack. Remember where they are attached and desolder them from the jack. There is no need to mess with the black wire from the battery. Next, there is a red wire going from the battery to the pick guard. Remember where it attaches and desolder it from the pick guard. Now the old pick guard should be free to remove.
Do the same in reverse to get the new pick guard in. Solder the red battery wire to the proper pick guard terminal. Poke the new green and wire wires through the output cavity. And solder the green and white wires to the proper lugs on the output jack.
So which pickup configuration do I prefer? I like them both for different reasons. The SSS has such a crisp attack and beautifully balanced pure tone. Alone in my room, I just want to keep playing it to hear the sound. But it was sometimes too crisp/clear to blend well with my particular band, which does pop-rock covers from 90's-present.
The Humbucker in the HSS is less pretty sounding. It's a little more cloudy with that typical midrange buildup that humbuckers have. But while it's a little uglier clean, it pokes the amp with the right frequencies for a tight overdrive sound. Compared to my PAF-style humbuckers, the midrange bump in the Cutlass humbucker seems to be more narrow and at a higher frequency. This produces a good tight controlled overdrive tone. Almost like a cocked wah sound but not that extreme.
But while the humbucker sounds vastly different from the middle and neck single-coils, the 3 pickups play together perfectly. I can set the amp to a moderate overdrive and "channel switch" from lighter to heavier with the pickup selector switch (neck light / bridge heavy).
Overall, I think the SSS is prettier sounding if you want clean to crisp mild overdrives. The HSS humbucker does big and tight overdrives exceedingly well but at the expense of an uglier clean sound from the bridge and a less authentic 'quack' from the bridge and middle.