What you refer to as 'automatics' are probably 'HST' style trannies.
For the most part.. people that use them.. bought them for a specific reason, and really like them. IE.. guys that do lots of loader work like them... guys that need to constantly vary their ground speed but leaving the pto speed the same like them.. IE.. mowing an obstacle course..e tc.
Any tranny needs maintenance... old ford gear trannies like you are used to a tough... lack of maintenance on them doesn't hurt them too bad .. If you treated a new HST like an old ford crashbox.. and didn't change the oil in it in 50 ys.. I'd expect the HST to not survive as well as the old crashbox...
Dependable over the long haul? Check back in 60 years!
Do they pull as well? Yes, no, maybee. Depends on what you want to do.
If you are running a big mower/disc/plow over an open 1000ac field And shift into gear and head out inthe morning and never touch the gear stick till evening.. I'd stick with gear. If you are mowing an obstacle course .. I'd get the HST. Pull as well.. here's one hitch... the hst has a relief valve... there have been a few posts here o fthe valve going into relief, thus wheels not spinning, thus tractor not moving.. it's not a super common occurence.. but is mentioned.. A gear tractor, you can assume will either slip the clutch, spinn the wheels, or stall... that's what I want.. Not a relief to pop... but that's my personal opinion... I am a gear man.
There are other small issues that can be mitigated.. like HST systems that have filters that blow out in cold weather .. but different oil and filters helps that..e tc.
There are some push-pull safety issues and 'extreme circumstance' issues that sit ont he edge of the fence as well. HST might be safer if you are working around a steep dropoff / cliff... IE.. more control of speed.. Gear tranny won't just plain die and stop moving if you blow a hyd hose.. plain gear trannied tractor might roll off a railroad crossing by judicous use of a pocket knife blade in a bad emergency vs an immobile HST..e tc.
Like I said.. far fetched stuff. For most issues.. you can do the same thing with either tractor.. one costs a bit less but makes your left knee work a tad more.. etc.
soundguy