Always had gears, this MX 5100 that I got a year and a half ago is my first HST.
Simple 3-range. None of the other bells and whistles like stall guard, auto-throttle, etc.
I brushhog about 250-300 acres. Year commercially. HST vs gear is like comparing a conventional rider today a zero turn.
The ability to slow down in rough areas or thick areas that would normally bog the engine.....and the ability to speed up in the smooth or easy cutting areas rather than shifting constantly...has been priceless.
The gearing in my old
L3400 I was constantly bouncing between 4L (3.5 mph) 1H (4.1 mph) and 2h (5.3 mph).
No more of that.
Grading, loader work, grapple and fork work....the HST wins hands down.
The fee times I wish I had a gear though...
Pulling the 3-14 plow, and pulling the 11' or so JD210 disc. Low range tops out at 3.7 mph. And has no trouble pulling either. But that's screaming at WOT. Medium range is a big jump to 7.3mph. tryin to run the disc or plow at 4 or 5 mph in medium range.....tractor didn't like it. Pulled the RPMs down to where I was going no faster than in low range. I have no doubt that a geared tractor with a 4 or 5 mph gear and this would have been no problem.
The only other time a gear would be nicer is in road gear climbing hills. Especially if pulling a trailer of wood