I agree with everything you have said here, and the rifle I had wore the same scope with Leupold rings and bases.I'll probably just confuse the discussion, but I like a scope to compliment the look of and balance with the rifle. That means gloss scope with a gloss blued rifle, of a size that doesn't overwhelm things and mounted low enough to get some kind of cheek weld on the comb. The 52R is a challenge because of the high bolt lift which as you've shown whacks the ocular end of the scope. My suggestion is to use a good compact scope that has a smaller diameter ocular assembly that builds in some bolt clearance. This is my 52R with a Leupold Compact 3x9 AO EFR mounted with medium Talley rings and bases. Everything clears and I think makes a very useable combination.
The OP didn't scope his rifle 20+ yrs ago, and other than resale of items, has no access to new high gloss Leupold's. How long has it been since Leupold offered gloss? Better yet, how long has it been since this rifle was produced? Or Kimber's for that matter. Going period correct could be a chore.
The OP is asking too much from one rifle, if he removed 100 yard bench, I assume BR, from his requirements, it would open up a lot of glass selections.
I am somewhat with the OP on concentrating on functionality over aesthetics here.
OP, not bashing you in any form, I just know thousands before me tried to build a hunting-target rifle, I tried myself and found the rifle did little justice to either discipline. Too heavy for hunting, too light and mismatched configuration for target< not BR either, just a LR steel blaster.