I have been quiet for a while but since I started this mess I should probably chime in. I do appreciate all the input and it has given me some good stuff to think about. I don't know that it has brought me any closer to my decision but at least I have more to go on.
A couple days a week I drive an all original Willys CJ3B to work. I would not drive it if I was in a rush. Its fun to drive when I am not. This simple thought is what made me decide to buy a new tractor and not an older one. As much as I love my old Jeep and as reliable as it is I wouldn't want to have to rely on it, or deal with it's issues when trying to work.
I kind of see the HST vs Shuttle debate as similar to the old automatic vs manual. Modern automatic transmissions are great but I still prefer my truck to be a manual for towing. Sure, it does suck in traffic sometimes but in the end I prefer it. Yes, the automatic would be easier to tow with but I just prefer the manual, mainly for reliability, even as strong as modern autos are.
That said, I sit in a similar place with the HST vs Shuttle debate. Just like lining up my manual transmission truck up to a trailer I want to tow is harder than it would be with an automatic, I generally believe it would be easier to inch forward an HST than it would be shuttle.
So, that is basically the summary of my thought process including what I have taken from this thread, if anyone cares.
Moving forward, while I have your attention, how reliable is an HST long term when pulling ground engaging implements? In the long run the bulk of my tractors time will be in the fields planting crops OR food plots. That is one of my biggest HST concerns is long term reliability issues.