Diesel Boy -
In addition to the other fine comments posted thus far - I'd also throw on one additional factor: warm-up time.
I know central Maine gets darn cold in Winter - a gear (tranny) would likely not require (much) additional warm-up than than recommended for the engine - the tranny oil doesn't get pumped around - it just lubricates.
I definitely take it slow on my HST for the first few minutes AFTER engine warm up when using my CUT in winter - as I want the tranny / hydraulic fluid to come up in temp (ie lower viscosity) some before going crazy. As my CUT is *mainly* a summer use (ie mower / hauler) - this extra time isn't a big deal for me.
While gears have been around for the longest time - a post (couldn't find it with search - but
HERE was a similar discussion) - had someone quoting 20,000+ hrs of runtime on a HST (non-tractor) with no major problems - so I think that in both cases (HST & gear) - that regular maintenance is simply the key to longevity in either case.
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Just to throw in my personal 2 cents:
I recently rented a larger, gear-driven Deere (4700) TLB to do some stumping - this was my 3rd rental of the same piece of equipment in 3 years - but the first since I've had my Kubota B7610 (HST). I had no problems handling it during any of the rentals - but now with 1 1/2 yrs on the HST - I preferred the HST for FEL work - being able to approach a load "at speed" - and then slow to a crawl to engage it - then zip backwards etc. - all without shifting. I had to "work" more (ex clutch) to control speed as I engaged the load - else I got jostled around a bit in my seat. (crappy gear-driving by a hydro-driver some might say! /forums/images/graemlins/wink.gif )
I do prefer the 3 gear-ranges of the Deere rather than just Hi-Lo of my Kubota - and feel the gear has "better" traction (ie better with ground-engaging implements) when trying to move around heavy items (stones / stumps) - and I like the "toe throttle" that the Deere has to increase the engine rpms whenever needed.
So I believe that - durability wise - all things should be equal - and the primary, intended task / job for your tractor should dictate which way to go.
Happy hunting!
Dan