New member, regular reader. Thought I'd jump in with a few thoughts.
I have 2 tractors: an old Kubota 6200 with hst and an older JD 830 gear with FEL.
As a homeowner, it really doesn't matter when doing FEL work that the JD is not hst. It's just what I'm used to. Now I'll admit, when i use my F-I-L's NH 555, I get spoiled to the hst real fast. But my JD gear, and I've noticed many others also, is designed where the forward to reverse shift is a straight motion. Quite efficient and no gear grinding when you're used to it.
I bought my 1984 model Kubota with almost 2500 hours on it. It was bought new by a mechanic who serviced it by the book. When I bought it, every light worked and everything was intact on the tractor, so it was obviously very well taken care of. I use it primarily for mowing. HST took a little getting used to. Let off the pedal and it's like standing on the brake on the JD. I never use the brakes.
All this to say longevity and dependability of a tractor won't be an issue with the average homeowner whether it's gear or hst. My tractors can take much more than what I normally dish out and yours probably will too.
If I were buying new, it would be a matter of $$$ and dealer recommendation. If the dealer (like one around here) didn't recommend hst for my use, I'd consider that because that may be a service issue down the road. Or I'd find another dealer.
Hope this helps.