I started out like you as a city slicker armature kind of like you. My opinion, is therefore willingly subject to correction by experts. For reference, I live on 5 acres with about 3.5 acres of open, level ground.
For your property I would consider a good, clean and well maintained used tractor. 4 X 4, from a major brand vs a Chinese tractor, water in the tires for weight, front end loader, and implements such as a 4' or 5' bush hog, PTO driven
chipper if need that can handle up to 4" limbs, and a 4 or 5' box scraper. With some shopping, $20,000.00 today should leave you some pocket change left over.
I live on the Central Coast of California where vineyards abound. It's probably unusual elsewhere, but here, vineyards lease new 4 X 4 tractors in the 25 hp range for towing trailers thru the vineyards. They are turned in each year to the dealers. The dealers in turn only sell these and rarely new ones in this size, because these are barely broken in. The dealers sell them at 50+ total hours with new frontend loaders. If they don't have 50 hours, they run them until they do.
In 2003, I purchased a 1998 JD 770 (790's replaced them the next year) from a private party that had purchased it with 52 hours. In 2003 it had 252 hours, a loader and a very old disc harrow. It has 25 HP (23 PTO HP) from a 3 cylinder Yanmar engine. The seller kept it inside as do I, and it still looks and runs like new. The seller told me I was the 11th call that day, and I purchased it at 10:00 pm on the spot. Later, over the years, I purchased a new JD 4' bush hog from JD, a used 4' box scraper from a used parts dealer and a 10 year old Bear Cat wood
chipper that had been only used once a year (with the original cutter blades in the original position). plus a 7' rake, and a new rear fork on which I put a home made 25 gallon 12' wide sprayer.
Other than routine service, I've put in 2 batteries (A Walmart Everstart lasted 13 years), replaced the two front tires and performed routine oil and filter changes and greasing; that's it. This tractor is not Hydrostatic, but with 8 forward and 2 reverse gears, one would think it has twice the HP it needs. It will run all day with a bush hog on 5 or 6 gallons of diesel. I burn dyed diesel so there is no road tax on it.
If I were you, I would not hesitate to find a good used low hours tractor, and look for used implements in good condition because many of them are overbuilt to last in commercial use. The major manufacturers (not just JD, New Holland or Kubota) have a tractor for every size and job, and they are pretty much bullet proof and economical to run and maintain. Also, older tractors may not need the blue diesel additive that many new one's require.
My results are in part because the tractor stays inside, the climate is mild, I always buy the largest battery I can find (It requires 550 CCA to start, but I buy one with 800 - 1,000 CCA). Since I'm old and have driven probably 600,000 miles in stick shift cars (including a 47,000 lb. school bus with a non synchro crash box transmission, the manual gears were not a concern. If I need to slip the clutch, which I don't do, I need a lower gear. I never try to shift on the fly on the tractor.
FYI: Tractor engine hours are not like a car. They are based on running at rated HP, not clock hours. Mine runs at 2,600 rated, about 2,750 max, so to get one clock hour at idle (about 750 rpm) it would have to run about 3.5 hours.
Before I bought mine, I looked at a lot of tractors that were in bad shape. They were pretty well run out and rusted, with rotted seats and tires. It may take time, but a good used one is out there. Your local Washington State dealers may also work with he many Vineyards in your area as they do here. You don't have to buy everything at once if not in your immediate budget.
If this sounds condescending, I do apologize.
Your friendly armature that was in the same boat you are now.
