Well cataract doesn't recommend even the oar rights to be screwed in, although I'm going to do exactly that on my cat oars.
I use the counterweights on the raft, and yes when teflon set screws strip strip they suck. I got a dental tool to pick out all of the shredded plastic, major PITA! But got new ones in and they are good. Those set screws aren't designed for re-doing often at all, pretty much once with a few adjustments if you are lucky.
In order to use the set screw on the oar right, I'm going to drill a pilot hole so it is really no different than the blade locking mechanism hole. I don't think crushing the set screws into the oar would be good, it will just start to deteriorate from there. Maybe it will be fine, maybe not. Even with the tape, it's going to take more force than just pressing into the tape to hold it, it will have to press into the shaft.
Why swap out so much? Get a set for each set of oars, I've heard people have even gotten cheapo ankle weights and duct taped them on. $15 vs $60+, seems not bad to me.
Living in Montana, boating in Idaho