I read through this thread quickly but skimmed over much of it so sorry if I missed something...
It sounds like you are a lot like me and that you want 1 machine to do all you'll ever need one to. having to maintain multiple machines gets old and costly. In my search for a small capable tractor, I had a list much like yours and ended up getting the LS xj2025 mainly because of the price and the capabilities. For the most part I have been mostly happy with it except for the HST seems a bit weak to me...
The HST, I would have loved to have the 3 speed hydro but didn't have the budget for the kubota.... or possibly even the gear tractor over the 2 speed HST. Having come from a gear tractor, there is no feeling like the power to the ground feeling you get with clutch and gears. but everything has its place in this world and at times I HATED my gear tractor and in the end, the HST has been better for my properties. However looking at your pictures, I would probably get the gear tractor for all that mowing.
Second thing BH & MMM, Again, at first I wanted a tractor that could do both, but the Kubota being out of my price range, I made the decision to just get the BH. I mow what I can with a 3 point finish mower and the rest I just get with a lawn mower. Your price for the LS with BH/MMM @ 23k seems extremely high. I got my xj2025 with the BH for around $17.5k cash deal. My dealer told me the MMM would have been around $1800 more if i wanted it. I am still contemplating buying the MMM because its not daily that Ii use the BH and changing out the bracket wouldn't be that much work.
Honestly though. You should just get what you feel comfortable getting and can afford. Buying something on someones advice has never been my way of doing things, although it can often help listening to what others have to say to avoid costly mistakes...