I'll throw in a new angle. Whats your time worth? When I am mowing my horse pasture, which has lots of trees in it, I bet I could save almost two minutes an hour if I had only gotten a hydro instead of shuttle shift. It takes me 3 hours to mow everything. I could save 6 minutes per mowing session, which I do six time per year. OK, I'm at 36 minutes per year of time savings for mowing. The other main use of the tractor is working up an indoor arena, where I can see no time savings. I saved at least $4000 by purchasing a shuttle shift tractor over a hydro. Spread that over say 10 years and thats still $400 per year for me to save 36 minutes. Thats $666 per hour.
Sure, a hydro would be nice, but in MY case, it just didn't add up. So take a serious look at the actual time that could be saved with a hydro doing the main tasks in which you need it to perform. Both systems can do the exact same tasks.
Operating a tractor with shuttle shift is easier than driving a car with a manual transmission. My wife has had absolutly no problems operation a shuttle shift, I seriously doubt you would either.