I agree with everything you have said here, and the rifle I had wore the same scope with Leupold rings and bases.
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.