Isaac, I think your 'overthinking' the problem. It's pretty straightforward from a practical point of view. If all the demensions are in spec, ie, no bore distortion/taper and proper piston specs then, no it probably makes little difference in the long run wheather you 'clock' the rings on installation or not. That is not to say I don't do it, rather mechanically, out of habit. My ring gaps are ~0.014" cold and, again, no I have not done a leak down on a cylinder with gaps alligned (to be honest, I probably won't either) Anyway, it'll have enough compression to start as static is 14:1 on the Mini and 15:1 on the Lotus.
At one time in my life I succombed to the 'drag racer mentality' and pushed the pistons in dry or on one particular 394 Hemi, used a fine 'jewelers rouge'...not these days. Now I liberally oil the cylinder AND the piston/rings before assembly. The new piston never runs on a dry cylinder and I have seen no unusual anything in the last twenty or thirty engines save a broken ring on a street Ford Fiesta 15 years ago.
[Another, sorta related question to explore...Why do I still run my engines in on paraffin based lube instead of just going to synthetic to start? The OEM's that use syn don't bother?]
"wear in the ring grooves Sorry, I have no idea whatsoever how groove wear can affect ring fitted tension. Wouldn't the ring fitted tension be the same even if the piston was entirely absent, and the ring was just sitting (properly oriented) by itself in the bore?"
Firstly (or lastly), ring tension is ring tension until the fire is lit...then, especially on Dykes or drilled pistons, the tension increases, a lot.
Secondly(or firstly) from my experience, when the ring groves begin to exceed a certain wear limit, expecially the top ring, blowby increases dramatically. I see it as a result of "ring flutter" whereby the ring no longer makes a square, perpendicular fit to the cyl. I come by this opinion from some tests I was privy to on some 'dykes ringed' versus 1/16" versus 1mm versus zero gap top ringed Cosworth pistons in a Lotus Twincam 1594cc engine many years ago (sorry, I don't recall the specifics of each type. I do recall that the Dykes and 1mm were about the same.) I have a set of JE's with 1mm's (for that 10,000rpm "one of these days" engine) and a set of Venolia's with Deves 1/16" for the vintage engine (run in quickly and last a long time). One BIG difference in ring type is overall bore clearance...the smaller the ring the more critical the fit.
Sorry this post got a little longer than I had intended.
Rod