I'm not sure if this is the right place for this post, so please feel free to (politely) suggest I take it elsewhere.

A couple years ago we moved from a house with 1/3 of an acre lot to this 15 acres, split between two lots. Our property is mostly wooded (primarily oak) with one lot being 10 acres of undeveloped land and the other ~5 acres where our house and barn are.

• The yellow circled area is the ~2 acres that are mostly cleared surrounding the house.

• The blacked out lines are the roads. Main road runs across the bottom of this pic, the other two running vertically are private dirt roads.

• The red area is ~5 acre lot our neighbor owns.

• The blue line is the lot line between our 5 and 10 acres.

• The pink star is around the area we're thinking about building our "dream home" someday.

• The grey line is our ~ 500ft long driveway.

When we moved here I had a push mower and walk behind snowblower, so I picked up a used '04 (I think) Troy-Bilt Pony/Bronco (not sure which), with two mower decks, a snowblower and a bunch of extra parts. It's worked alright, but I keep running into situations where it feels like it's just not quite up to snuff. The snowblower bogs down on my snow and I end up spending all day working on clearing snow and unclogging the auger. Or the insane amount of leaves end up piling up and jamming in my mower deck's belts. Parts breaking that I then can't find replacements for. etc...

It seems like part of the problem is that the guy I bought it from was a little bit of an "innovator", and I'm not even 100% sure that everything that came with/on this thing is meant to.

Basically, where I feel I'm at is that I have 3 options:

1. I pour a bunch of time and effort (and probably money) into getting this thing fixed up and running like new.

2. I get rid of it and replace it with a new "garden tractor" in the same class.

3. I upgrade.

Option 1, is pretty much out of the running because I'm a new dad for the first time twice over this year so I don't have the time to add another project.

Option 2, feels like it's probably the "smart" and economical choice. But I worry that I'm still going to be fighting the issues I've had with belts slipping and feeling like it's underpowered for things I need.

So I'm leaning option 3, but I have next to no knowledge on these things. I have no clue how much I actually need. From my minimal research, I think I want to get a subcompact or compact tractor. I'm leaning toward Kubota, and they've got some good financing options available through the end of the year. I can compare features and HP amounts, but have no real world understanding of what any of it really means. Any advice on what to get?

My main uses would be mowing the 1.5-2 acres of grass (and acorns & oak leaves) around the house and clearing my driveway of snow. Occasional use would/could include clearing some thicker brush in some areas, possibly digging up a garden plot (would probably rent implements if that's a thing), clearing an area to build our new house eventually and just other random landscaping needs.