Welcome to the gauntlet of tractor buying decisions!
I'll throw in my $.02 about Kioti's & HST.
HST - Without starting a holy war, here's my take - if you are doing a lot of back & forth movement, HST is generally more straight forward - meaning there is less for the operator to do & it is therefore easier for a novice to pick up quickly. By saying this I am in no way saying that "experts" don't use HST or that you can't be very efficient with a gear based transmission. If you are going to do lots of traveling in one direction at a constant speed (e.g. mowing), I see the HST loosing a lot of its advantages (e.g. if you aren't changing speeds or directions, you don't have to change anything on a geared tractor - just like an HST).
I've seen an operator run a shuttle-shift tractor w/ a loader just as fast as a good HST tractor/operator. The thing was that the operator was very good on the shuttle-shift. I guess I think of it like people who drive standards vs. automatic cars - nothing is wrong with either transmission type, and they both have +'s & -'s. You put a good driver behind either and you'll be hard pressed to tell the difference watching them from the side of the road. I've operated both and don't have any problems or issues with either. It's just a personal preference thing.
Kioti - I think you'd be hard pressed to find a Kioti owner who thinks their tractor is in the "YUGO" class of machines. I seriously considered a Kioti. I haven't owned one, but based on looking at them and reading posts here, I think they are a very high quality of machine - if anyone says they have bad fit/finish, they haven't looked at them close up. Where it appears Kioti has had issues in the past is dealer/parts network, but this doesn't apply to everywhere. In my area (Texas) there seem to be quite a few Kioti dealers & good parts supply - but this may very well not be the case in, say, South Dakota. It just depends on where you are I suppose.
If you determine that HST is a requirement, that will essentially kill off the Kioti (they don't offer it). But, that being said, if you are considering a shuttle-shift transmission, I think that you should look into Kioti a bit more. Again, I'm not saying that it would or would not be the "right" choice - I'm just saying it isn't the Euro-junk you might think it is.