go for it . i have pulled a velkie single with my toro32 for years w/no prob. some times you have to get off going up a steep incline. make shure you install the chain hook that comes with it. its very handy
I pulled a 2 wheeled with my 48" belt drive. There is no difference in the trans. if I am correct. Either way hydro or belt u should be fine. Turning might be a pita with a 36" though. My 48" had enough overlap on the deck that I could just make the turn w/o backing up or missing grass.
50/50 on the usefulness. There are some lots where it does not work because of the backing up. But if that is your only mower and you use it on bigger lots also than it will work fine. The single wheel is better too back up with. As far as working the mower too much -I have a 48 belt drive that was my first mower. 15hp and the thing still works fine with over 1700 hours on it (most with velke in tow).
All our other mowers are hydro with 15- 17- and 19hp on them and they all show no sign of wear because of velke use, both single and double.