Hey, congratulations on finding your tractor. I completely agree about going larger. If it is maintaining land that you are doing then larger is the way to go.
We've had quite a few tractors over the last 50 years. I don't blame you for wanting HST...or for finding that you enjoyed the way powershift works. HST is slightly more convenient for loader work and powershift slightly better for tillage, blading, or pulling. We've had both - or I should say all three to include gear shifters. Most recently we've had powershift on the 33 hp Yanmar and the 90 hp JD and HST on the Kubota. The other Yanmar and the JD are gearshifters. I like gearshifters too, but find powershift and HST offer much more operator comfort than the old gear shifters.
Gotta throw a bone to the gear shifters out there, because there is one area where straight gears and a clutch are better and always will be - and that is in instances where you need very fine control over power and movement....when you are moving scant inches under load and need to control the power very precisely. Gears and a manual clutch just cannot be beat for doing that.
On 3pt hoes. We've had a few of those as well. Be SURE to check if your tractor's 3 pt has any form of automatic lift. An automatic 3pt lift is often called "Draft Control" and most larger tractors will normally have that feature. You must turn off any form of draft control before using a 3pt backhoe. This is very important. It is the single safety downside to a 3pt hoe but it is a big one. Ask your dealer. You'll have to to find a way to make sure you do this. I forgot one day and what happened that morning still scares me.
On makes and models of tractors....we are lucky to live in an era with so many good tractors. It's not even a matter of good versus not so good. They're all good. It comes down to the intangibles.
Your story sounds a bit like ours. One day my wife decided that we should have a nice new tractor instead of another used one. It would be one that came with everything new and working properly so that we could work with in instead of on it. The resulting search took months and ended almost by accident with a stop in at a dealer I'd always passed by on our way to the "real traditional tractor dealers". The result was a new M59 Kubota back in 2008. It is now a member of the family. One of the best investments we ever made. All those trouble-free years!
Enjoy your new tractor. Please do learn how to post pictures!!
rScotty