.....Just back from a camping trip. Lets see what I can add, if anything.
Limiting your search to those two brands...Seems wise to me. Both are good. Kubota would be my first choice in the small/medium size tractor just because that is their area of concentration.
Dealer New vs Nice but Used? It all depends on the person doing the selling. You absolutely need to have someone you trust on your side to give you advice and help with this search. And that person needs to to be there in person. If you have such - neighbor or relative - and that person understands mechanical things, I would have no qualms about buying used.
You should be able to find an excellent machine in your price range. That is a reasonable price and should get what you want. You want something wide and stable. It should have a front end Loader, 3pt hitch, 4wd, power steering, and be in nice condition with under about 1500 hours and not over ten or so years old - though he age is less important than the condition. HST would be a bonus because HST makes a tractor so easy to use. A well maintained used tractor like that should last a lifetime with little or no repairs. Maintenance and condition are the keys.
If looking at used, make price secondary. What you want is one that the previous owner appreciated and enjoyed.
I don't know anyone who faithfully follows all the maintenance in the owner's manual. But try not to get too far behind. Frankly if I keep to half the factory recommended schedule that feels about right to me.
BTW, weather is hard on tractors. A shed is best, though I use a lightweight treated tarp covering the tractor down to about half way down the tires. Not perfect, but sufficient. It keeps sun and moisture off while letting it breathe. Cover it every evening and tie it at the corners so it doesn't flap.
Yes, you can get by without a tractor. We did on our place for years. Almost anything a tractor can do you can do with hand tools and manual labor. It just takes longer.
The big exception is picking up something heavy and moving it. That is what the front end loader does, and for us that was the most important labor and body saver.
Good luck,
rScotty
This is excellent insight, thank you for your reply. Also, hope camping was fun!
These basic tenants are a good break down for something to look for. I have a 2 car garage that houses my mower and believe a tractor would fit in there next to it.
As an update for anyone interested, I did talk to my dad about coming with me. Due to hours of operation of some of these locations and my own work hours, I'm going to have to get a day off from work to visit the dealers in person.
For context, he's not mechanically savvy but seems to have become obsessed with the
idea of tractors, wanting one of his own (just doesn't have the space nor right property for it) and watching YouTube about them for the past year rather obsessively.
He did, however, convince himself that it is not a tractor I need, but rather, a skid steer. Probably out of my budget at the cursory glance (woah so expensive), but I would love everyone's thoughts on the matter. Clearly, you all are tractor people, and I am stubbornly in the position it is a tractor that would suit the different needs I have - and falls more within my budget. And I just like it more? I don't know. He seems more caught up on the lifting power of a skid steer, which I don't think is really the point of this purchase for me personally. I'm not going to be moving pallets of bricks around construction sites.
What are your thoughts on a tractor versus skid steer?
Also, questions about wood: it's manageable right now. I think, if I had a tractor at my disposal today, I would have used it to move about 30 split logs from the top corner of my property to a burn pile rather than carry them. I think that would be the extent of it. If one of the big firs that I had around me were to catastrophically fall, then...I would probably chainsaw them up to manageable pieces to move them and also, probably get hired help.
The question about brambles: I've done a pretty okay job with managing them with a heavy duty weed wacker. Just blew out the clutch on this today annoyingly when I caught it in a buried steel cable though, so no more of that until I fix it (which, now thanks to you folks, I am going to fix it myself

). If I keep them under control, that's all I would need to do - that being maintenance. If I don't, I would need to cut them back with a powerful implement. The location of the brambles are now in tough ledges built out by rocks, along fence lines, and around a pit that the previous owners were using to burn trash (that I have now removed the trash and need to fill the hole).
In addition, what is your position on a brush hog versus flail mower - another distinction that my dad asserted was better - and I didn't have enough information to refute other than a brush hog was the implement that was always used when it was cleared.
Thank you everyone for the insight and discussion. I'm reading through everything that is being posted and am learning so much!