I grew up on geared tractors beginning with an old 8N and still have some. I also have HST's as well as a M8540 with Hydraulic Shuttle Shift. The Hydraulic Shuttle Shift is a vast improvement over my old synchro shuttle shift which was an improvement over non shuttle shift, but synchro transmissions which were an improvement over the non synchro transmissions.
I have to admit that having used them all or many different ones anyway that I prefer the HST. I think it is much easier for the novice or less experienced user to operate one efficiently; my wife whose only tractor experience has been on SCUTS, JD2305 and a couple of BX models, can bush hog with my
L5030 while I do so with my M8540, she won't go near the 8540 or our old CX80.
With many owners using their tractors for relatively small numbers of hours, my used
L5030 was seven years old when I bought it with 700 hours, it is going to be hard for many to get really comfortable with geared units no matter how good they are. Now that is different for high use people as our renters and friends can do stuff with their 8000 Series John Deeres I wouldn't try with my
L5030.
My only advice is get what you want or you will buy twice and try them all out. Keep in mind, like a recliner, a short try out can be misleading as what you "think" you can get use to or will grow on you most often won't.
Not knocking anyone's preference; just what works best for me.