Wow, a lot of dissing the HST, which is fine. Here's my two cents.
I bought an MX5400HST. I bought HST because (a) it sounded a lot better for noobs, both me and my wife, and (b) it sounded a lot more convenient for loader work.
I use it on a very steep hills. There are basically two (of my own) rules I have developed for going up steep hills:
1. Be in 4WD.
2. Be in low gear.
Again, this applies to steep hills, or moderate hills under load (say, a bucket full of rocks pulled out of those hills). I have never had something I couldn't traverse in low gear with load. (Also: cue the Messicks video about use of the HST throttle w.r.t. gearing, sorry, don't have a link).
I have no issues with the tractor at all when I follow those rules.
That doesn't mean I never use higher gears, normally I'm in medium gear for most everything unless the hill is steep or the load is high. Even then, a bucket full of gravel is fine in medium just moving it along the driveway.
The only time I've ever wished I had more power is when lifting with the loader, mostly when I'm trying to get rocks out of the ground, or bust up a pile of dirt/rocks that has settled.
Love the convenience. Love the precise control, especially on those high-pucker-factor hills where I want to go v_e_r_y s_l_o_w_l_y.
I've read things here about how HST is probably better for stump grinding uses, where you need to move slowly, but can't speak from experience.
Anyway, not saying it's better or worse, but it's working for me. Would I have been equally happy with gears, maybe, don't know. Other geared vehicles/motors are fine, but I'm not unhappy I spent extra on the HST tractor. The control is great, and there's a lot less to explain if I want to convince my wife to try it (though I haven't done that). Using it is dead simple.