Frank,
I think you answered your own question, actually. If the performance issue is just cold compression for starting and ease of handling, then it is the fit. Your current example appears to be the OS 46SF which should have a single, standard ring. This is a tension ring which is part of the key to success. Other engines, perhaps your HPs(?) have a Dykes ring which is a different animal, and may have poor compression if flipped by hand but still run great. I've got a few K&Beast 40s with Dykes ring that can fool you.
Here are some thoughts:
Some experts are more expert than other experts. Proof of expertise is in the results. Everything else is just talk....
If you don't run an engine after you set it up, then you have to be really good at it to know that it will work fine. Lesser experts and more cautious engine builders who value their reputation would run it to make sure it will seat and not bind, and that the ring has acceptable temper and doesn't go "flat" after getting it hot. I got a couple of ringed engines from Frank Bowman, and he ran both of them after he completed his work. So he could be very, very confident that the setup was right.
If all the parts are really good--like factory new--and really to tolerance--and now you have to fit a ring to the engine, that takes skill but is not hard to succeed if you can make a ring to fit your parts. That means lapping it to width as needed and gapping it for leakage and to prevent seizing. Taking one out of a package and expecting it to work great is probably a little optimistic.
If you tell someone "to just change the ring" that can handcuff them. For example, if the installed liner is not round, then you can screw with the ring all day and be disappointed in the results. If the liner is ok, but the case bore is not round or is otherwise damaged, then the liner will conform to that and again, ruin your chances of a good fit. Engines that hit the ground hard may no longer have straight cases. I "repaired" an Enya that was like that.
If the metallurgy on the ring is not right, it's not going to be a good performer. On a tension ring (I think the SF falls in this category, but I don't own one...) the ring has to have a larger diameter than the piston, but not so large that the friction is too high, etc. I don't know how Frank was making his rings, but the ones that I made years ago were machined to a very specific larger diameter before they were slit. That gave me an initial tension setting. Making a ring the ID of the liner and then "opening it up to tension it" will almost certainly make it oval shaped. This doesn't work well in my experience. It is the last resort of the desperate, the night before a contest, with no spare rings in the drawer....
I suspect that a lot of engines are using fine-grained cast iron rings. (Meehanite) Maybe there is something more modern being used.
Excessively rough finishes on the ring or on the cylinder will prevent it from ever seating. Not prepping the cylinder before putting in the new ring seems like a waste. At best, the results would likely be hit and miss.
I found that pinned rings are harder to set up. Harder to measure the gap accurately.
Trying to run a chromed ring on a chromed cylinder used to be a fool's errand unless someone has invented some magic. For example, if the fit was so perfect that it did not need to wear at all to seat--that would be magic!
You probably know all this already, being a ringed engine man. And I didn't really help you. But we can always commiserate, right? That doesn't cost extra.... And that is good therapy.
Dave
PS--My last "project engine" was a friend's K&B 61. The last engine man abused it for sure, but probably the one before that did some fundamental damage to the case bore and the liner. I did what I could but after getting rid of the pliers marks on the liner flange and the huge burrs on the inside of the case from a broken ring (improper disassembly) I will probably have to buy and fit a new ring. If the liner fully springs back to round after heat cycling it there is a chance.... I won't know until I run it. But right now, the compression is poor.