There is no HT HSS, the HT Cutlass are only SSS. A the standard HSS Cutlass has a two-conductor humbucker, permanently in series, coil split or parallel are not possible. And yes, position 2 is not quite as bright and less quacky compared with SSS. It's close enough for my purposes but not everyone agrees (including your good self).
A Chopper really should be in series, at least in position 1. That's the humbucker sound. If you go parallel, it will be bright and thin and output will drop. I have disliked any humbucker I have played in parallel because they usually sound thinner and weaker on their own than a standard single coil. But in combination with position 2 it could be fine. I'd suggest two options...
1: Add a DPDT mini toggle switch to the pickguard to switch the Chopper from series to parallel. Send the output of that to where the Chopper is currently connected to the 5-way switch. No silent circuit or phase issues to complicate things. Easy job for a good tech.
2: A 4-conductor humbucker can be in series in position 1 and coil split (single coil) in position 2 for combination with the middle pickup. Google "HSS autosplit". It's a simple mod with a standard 5-way switch BUT because of the silent circuit on the Cutlass, I suspect a 4-pole superswitch will be required. BUT the two coils of the chopper are very asymmetric (green-white is 5kΩ, red black is 3.8kΩ). So you'll have to use the green white coil for position 2 but and silent circuit will need to be disabled for position 2 and there is a possibility of phase issues with the single coils which would require a substantial re-wire of the circuit to get right. It's doable but I don't know how good your tech is with this level of electronics, or how expensive they are.
