I'm afraid I don't see the problem. I've been playing classics (slotted headstock) since 1955, changing strings whenever necessary—every few weeks, if I'm playing a lot. Granted, changing strings is one of those semi-tedious chores, but I'm afraid I can't see what the problem is.

The real trick on a nylon-string classic is getting a secure (and neat-looking) loop-knot on the bridge. With a steel-string guitar and barrel-ended strings, simply poking the string into a hole in the bridge and stuffing a bridge-pin into the hole to hold it in place is duck-soup. It seems to me that all you do at the headstock is stick the string through the little hole in the peg, loop it back a bit so the next wind holds it in place, and crank on the key until the string is up to pitch. Same thing, whether the pegs are sticking up through the headstock, or in slots like on a classic.

Don Firth