You're right about the difficulty of changing headsails. Almost makes me regret going from hanks to a foil. Headsails with hanks were relatively easy to change compared to sails in a foil. Seems some of the big maxi boats are going away from roller reefing to hank-on sails.
My current headsails? Largest is a 150%+ full hoist racing mylar 'funny sail' - add a crew member to trim it over the lifelines during a tack. This sail won't furl or reef. Next is a 135% LP (80% hoist) which seems to be on most of the time. It was made by North but finished by Farrar to fit my T30 (special deal). Originally had no luff foam or ropes, and was baggy when reefed to 110%. Took it back to Farrar for foam, but he added ropes - not sure if I'm happy with them. Third is a 70%LP 70% hoist 'chicken jib' from 11.5 oz cloth - you can bounce cannonballs off this thing. I've had it up in 40+ knots and its beautiful! High clew so it trims onto my existing track. This sail will reef/furl, but I've never reefed it. Probably should have gone with a 90% with the idea of reefing it to 70%. But then, I know I can reef this one to 50%.
Experience says: You get in more trouble with too much sail than with too little.