You seem to know what HP you want/need... but as or more important is the size and weight of the tractor. My first small tractor was the Kubota
L2501 - which was really a wonderful tractor but most importantly, it allowed me to really learn what I valued/needed after having used it - rather than just reading everything I could until then.
I was relatively brand agnostic when I looked to upgrade the
L2501 and I created a LOT of spreadsheets comparing the specs of various brands and models. Dealer proximity and capability are important attributes, but frankly I wanted to buy a tractor that I never would have to go back to the dealer with. As for parts and maintenance items, the internet has served me well.
I ended up purchasing a Kioti DK4210SE Cab model and I couldn't be happier. 250 hours on it now and I've never had a single problem or issue. I'd recommend considering to move up to the DK series given how large you property is and the uses that you have described.