Lawn mowing is the big decider. Questions that go with that:
- Do you want mid-mount or rear mower? Often whether your better half will drive it influences - mid mount can be easier for those who don't drive tractors often. L doesn't have mid mount (well, Grand L can, but that's a big lawn mower)
- How fussy about your lawn are you? If you're quite fussy you won't want a large tractor driving around and ruining it. But that can be a compromise in terms of capacities for other tasks - for an 80 acre farm usually an L would be the starting point and maybe an M
- How much mowing? If you're mowing 5 of your acres, then a bigger machine with a large rear finish mower is the deal, if your mowing is fiddly and around an acre, a mid mount is good
- If you're not super fussy about your lawn, and want to do a bit in your pastures too, a rear flail mower can do a bit of both in a reasonable way - you can treat them mean more than you can a finish mower, but you probably wouldn't mow brush with one. GP outdoors did a video on his youtube channel of a flail mower on his small B
Moving pallets - on the front or the 3ph? If the front, you probably want a quick attach. They're not as common on older machines. I personally use a 3ph mounted set of pallet forks, and they do most stuff fine, I just can't lift pallets high (like off a truck - but I can with a loading ramp...)
Ditch digging with a backhoe, or ditch digging with a FEL? Lots of opinions on back hoes and whether they're good value for money.
Cab or not. Snow plow or not. Those are important questions.
With elevation turbo models can perform better, but you're not that high really. Or you could get a higher horsepower model to start with.
Taking a stab at all that, I'll guess you're not trying to make a bowling green, so a small L with a rear flail mower, a set of rear pallet forks, a FEL. Consider a grapple if you're moving logs and tree trimmings. Borrow or rent a backhoe if you really need to dig ditches - it's not that often usually and sounds like your neighbours have machinery you can use.
Consider an L2501 (a new machine). They're good and not too expensive, they may be price competitive with an older but slightly larger machine. If you're a mechanic I'll assume you can fix things, but that doesn't mean you want to fix things....