I think like most every question related to what tractor or features to buy, it boils down to what you plan on doing. As you can see most of the opinions are based on what people have and what work they are doing.
I think we can all agree for light to medium use the HST is plenty reliable for a property owner. If you're set on a JD, I reccomend finding a manufacturer's rep. or get a hold of a technical rep. for JD. Usually the technical reps. don't care at all about being salesmen and will give you the straight poop.
I first bought and still own a gear tranny. I actually feel it is safer to learn on, since you think out each move when you're learning the controls. When on an HST I tend to be a little lax in the safety and thinking ahead department (hit it and go). Now, shifting gears is not a thought and when mowing, raking, blading, tilling or hogging I wouldn't consider the HST a big step up in convenience.
BUT, when it comes time to need a loader for a continuous stretch, I have my brother come down with a shuttle shift. Even the shuttle shift gets bothersome after a while, and I would kill for an HST.
Large construction equipment has been running HST for many years. I have to imagine that the HST is more maintenance than a geared tran, but these are production machines and need the speed of HST to make money. The additional cost of maintenance is offset by production. Not the case with most of our 'backyard' tractors.
The John Deere website has 'question email' page on it. Start asking there and keep pushing until you get a good answer. I would be curious to see what they say.