I've had the same "difficulty mounting" my tubes as my tubeless with the modern rims. I've had trouble getting the tubes tires to pop on all around. I did get a few tools which help. This big screwdriver made for it, then another tool to help guide the tire on rim. (same problem tubes or not). I also got a $60 air canister(used w/ my pump), unused yet, that I'll be using next time i need popping help. As far as repairing tubeless on road, i carry a tube, but i haven't needed it. I'm not convinced about tubeless, but i'm going with the flow. I may even try tubeless on my road bike, probably after the 3rd or so flat this summer.