Interesting ideas... thanks for posting this.
I agree that the glass is a total waste of time. If you do the "wrap over the leading edge" method, there's really no danger of warpage anyway, because the fins have glue (and thus moisture) on both sides simultaneously, and therefore any tendency to warp is "balanced out". And, as you correctly pointed out, the glass cuts off virtually ALL the routes for the moisture to escape from the fin and allow the glue to dry... My first experiments in papering fins, I used some stacked books, but like your experience, they slowed the drying progress considerably (not as bad as glass would I think!) After that I papered fins without it and no worries-- the dried fine overnight and no warpage.
On the "tumbler as rolling pin" idea... I think this is part of your problem-- the REAL TRICK to papering fins is twofold-- 1) you have to use a VERY THIN layer of glue-- it should be "sticky" after applying it, but NOT WET... if it's wet, you've got TOO MUCH glue. I know, you'll think, "this little bit of glue can't POSSIBLY bond", but it DOES... (so long as you put the balsa and paper together immediately after spreading the glue out very thinly-- I personally just use my index finger to spread the Elmer's Glue-ALL (white glue) over the paper, and when it starts to feel more sticky than wet, almost like it's about to stick my finger down, that's when I push the fin down onto the paper firmly, and start applying the glue to either the upper surface of the fin, or to the opposite tracing of the fin on the paper above the leading edge... I don't bother with "spatulas" or credit cards or anything because in my experience it's too hard to get a VERY VERY THIN layer of glue... they tend to 'float' more and leave more glue behind, PLUS, your finger is warm-- it helps the glue to "dry out" a bit and tack up when spread very very thinly, and you get the tactile feedback of when the glue layer is JUST RIGHT.
Using a tumbler as a rolling pin is creative, but I think it contributes to your problems, honestly... A glass is a VERY large diameter object, and larger diameter objects generally exert less surface pressure than smaller diameter objects (or the larger ones spread the force out over a MUCH larger area). The second REAL TRICK to papering fins is, once the paper is applied, to BURNISH IT DOWN VERY TIGHT ONTO THE WOOD! You want to squeeze out absolutely ALL the excess glue from between the paper and the wood... don't worry, enough will remain to lock the paper down onto the wood permanently... To really do a GOOD job burnishing the fin down, you need a SMALLER DIAMETER burnishing tool... I've found that a regular old gray and black-capped Sharpie markers works WONDERFULLY well for burnishing down the paper onto the fins-- the surface of the marker is rounded, but small (maybe 3/8 inch diameter or so) which is IDEAL for applying pressure to the fin... and there's a technique to it... start from the CENTER of the LEADING EDGE of the fin, and work OUTWARDS AND BACKWARDS across the surface of the fin, holding the pen flat against the fin, and simply SLIDING it across the paper towards the back and root and tip edges of the fin... you DON'T have to "roll" the fin, although you CAN. If you use too much glue, the paper will get "wet" and be VERY soft and prone to tearing or wrinkling... that's why a THIN coat of glue is absolutely essential. Even when you think you have the glue layer "too thin" when you stick the fin down onto the paper, or fold it over onto the second half of the paper, you'll be AMAZED at how much glue you'll squeeze out with a PROPER burnishing job... It's basically the same process as floating out drywall mud or putting up wallpaper-- you want it to be worked down TIGHT against the wood, to eliminate all air/glue bubbles and to ensure a good TIGHT bond to the wood (the thinner the glue layer, the stronger the bond, in glue joints... it seems counterintuitive, but it's true!). Once you burnish the entire surface of the fin, flip and repeat in the same manner on the other side of the fin. Once I've finished BOTH SIDES of the fin, I then run the ROUNDED TIP of the Sharpie marker, opposite the cap end, over and around the edge of the fin, all the way around. I cut my paper to have at least a half-inch of paper all the way around once the fin is covered in paper... (except the leading edge, which is where the fin is folded over onto the other side of the fin to paper both sides at once). This burnishing the paper over the edge does a couple things for you-- it ENSURES that the edges are LOCKED DOWN TIGHT against the wood, and the glue that's squeezed out from between the wood and paper that's trapped in this area is evenly spread, and glues the paper to itself, ESPECIALLY if you airfoil the back edge of the fin (taper it down to the classical "teardrop" airfoil). The paper will be glued down to itself TIGHT, completely locking the fin inside the paper, and in the case of the trailing edge, this will be a benefit later when we cut the excess paper off the fin, because we can leave a TINY STRIP of the paper glued to itself just past the edge of the wood to ENSURE that it stays locked together, if we desire, or we can cut it off flush with the back edge of the fin if we want... up to you... Be sure you flip and BURNISH THE EDGES ON BOTH SIDES OF THE FIN... don't worry that it'll end up "flat" on the table on the opposite side you just burnished, while the side you're burnishing presently will be curved over the edge of the paper... it all balances out while drying and the paper will be stuck down TIGHT over the edges when you're done...
Now, SET THEM ASIDE TO DRY COMPLETELY... I notice you said you started cutting off the excess paper right after applying the paper, after rolling them under the glass... Honestly I'm pretty sure THIS is part of your problem too... wet paper doesn't cut worth a darn, and messing with them at this point is just going to mess something up, not make it better-- you've applied the paper, got it burnished down TIGHT with an ULTRA-THIN layer of glue, now's the time to let the adhesive do it's job, and set up, and lock everything together permanently. I just set the fins aside, leaned up against the kit box overnight to dry, in most cases... the excess paper won't hurt ANYTHING at this point, in fact, it works in your favor, due to the burnishing around the edges, gluing the paper to itself.
The next day, when the glue is TOTALLY dry, THEN use scissors to take off the excess paper down to about 1/4 inch or so of the edge of the wood, then CAREFULLY SHAVE the rest of the scrap paper off the edges down to the wood using a SHARP hobby knife... Go slowly and carefully, and you can shave right down to the edge of the wood in one step... if you're afraid you'll nick the edges of the wood, shave the paper off down to within about 1/16 inch of the wood, and then go back and, resting the side of the blade against the wood itself, carefully shave off that last 1/16 inch of paper by cutting toward the wood... if you have a sharp #11 blade, it'll shave off in a pretty little curly-Q pretty as you please, easy-peasy... Decide how you close you want to shave the paper to the trailing edge, and then carefully shave that down as well. Shave the paper down completely to the edge of the wood on the tip and root edges of the fin.
If there are any "hairs" or bits of paper or glue that didn't quite shave off cleanly, holding the fin edge against a sheet of 220 grit sandpaper on your workbench and, tilting it at a SLIGHT angle to put the contact with the sandpaper precisely on the fin edge, with slight downward pressure on the fin, draw the fin towards you a time or two-- DO NOT sand "back and forth"... do it like you'd sharpen a knife-- in one direction ONLY, draw the fin toward you, lift the fin and go back to the opposite side of the sandpaper, and do it again... inspect, and repeat until the edge is as clean as you want, and repeat for the other side of the tip edge and root edges, and you can similarly dress the trailing edge if you desire...
I notice the paper doesn't go all the way to the root edge of your fin-- I take it you "pre-cut" the paper to leave the edge more exposed for filleting?? I've found that's really not necessary and complicates the papering process... paper is, after all, wood, albeit reformulated wood... and white glue is compatible with wood glue used to attach the fins to the tube and the structural fillets (and with TMTG if you're using that for fillets as well). Well burnished-down paper glued to the fins will hold a fillet just as strongly as if the yellow glue or TMTG were applied directly to the fin wood itself. I've had a papered fin (edge to edge papered-- no exposed wood except on the root face and tip face of the fin) glued to the tube with yellow wood glue and filleted with TMTG go squirrely on an upper stage flight one time, and hit the ground at a high rate of speed UNDER POWER, basically coming down horizontally RIGHT ONTO THE EDGE OF THE FIN, and it ripped the fin off the rocket, alright-- BUT IT TOOK ABOUT HALF THE THICKNESS OF THE TUBE WITH IT! Also, this glue joint did NOT fail until the outer half of the fin and paper were ground to dust from the impact before the tube wall itself FINALLY gave way-- the GLUE JOINT DID NOT FAIL!! When your glue joint is STRONGER than the paper tube to which it is applied-- well, you cannot get any stronger than that! (it's pointless to try for "stronger" because, like the chain, it's going to fail SOMEWHERE, (at the weakest link) and so long as the glue joint isn't the weakest link, that's all you can ask for... BY THE WAY, these were DOUBLE-GLUE JOINTS... another procedure I HIGHLY RECOMMEND!)
Now, I hear ya, that you want substantially STRONGER fins than balsa alone... balsa is notoriously soft and easily dinged, dented, or crushed... and paper adds some strength, but only so much... You have a couple choices...
One is, going with THICKER PAPER-- switching to 60 pound or 110 pound cardstock instead of regular 20 pound printer paper should add considerable strength. Might make working the paper down a bit harder though, but it should also make a harder surface VERY resistant to balsa dings...
OR, you COULD CA the balsa fin BEFORE papering-- as you said, lay down a layer of wood glue along the root edge and let it soak in and dry (the first step in double-glue joints BTW) and THEN soak the fin with the ultra-thin pink bottle CA, let that cure, and THEN paper the fin... I've never tried it this way, but the white glue SHOULD hold the paper onto the fin in the same manner-- probably not AS strongly, but if the fin isn't sanded, the CA tends to raise the 'balsa hairs' and dust and crud on even the most meticulously cleaned balsa surface, and should provide plenty of "tooth" for the white glue to lock the paper onto the fin (so long as the "grit" from the CA doesn't show through, but I think that's unlikely... you'd have to experiment here to do see how that works...
The other alternative is, paper the fin normally as I described, then, once it's completely finished, THEN drench the surface of the PAPER with CA... the CA should soak into the exposed layers of the paper and the edges of the fin (especially the tip and trailing edges which are exposed-- again, presuming you have already applied wood glue to the root edge and allowed it to dry as the first step of the double-glue joint to glue the fin onto the rocket later). The CA should harden up the surface of the paper into a composite material something like fiberglass, on a smaller scale-- instead of glass fibers and epoxy resin, you have paper fibers and CA resin... just the same way you'd harden up a paper shroud or transition on a build by soaking it with CA...
Of course, balsa will always be balsa... we can "harden" it with CA, but it's just flat never going to be as strong as something harder... even papered... if you're REALLY wanting a hard fin material that will be the MOST resistant to crushing or dent damage in flight or landing, you should probably just switch to basswood and call it good... basswood is MUCH more resistant to crushing and dinging and denting than balsa will EVER be, no matter WHAT the balsa is treated with...
I'd give these techniques a try before I really passed judgement on the whole papering thing-- there are reasons why some things work better than others... and if you want a more 'dent resistant' surface, well, you may have to experiment even more to find what you like...
Good luck with your projects! OL JR