I spend a lot of time hooking up stuff and the HST makes things tolerable. I think I have less leg cramps because of the HSTs But if I were out doing long stretches of ground contact work I'd want gear.
/ New to Forum and less familiar with tractors...Hydrostatic vs Synchro Shuttle
HST by all means. My soon to be eight year old granddaughter drives my little Kioti all around the house. Push the pedal to go, let off to stop, push back of pedal to reverse. Your wife and kids will operate it easily.
The only advantage I see for a gear drive would be if mowing large fields.