I have a very similar sized tractor to you. On about a tenth of the ground. Now, acreage isn't everything. You need to list out your tasks and figure out how large of a tractor you need to do the majority of them with reasonable efficiency, with the understanding that anything that you can't do with your tractor you'll need to rent equipment for/hire done at some point.
I would not want to deal with 20 acres of pasture with a 5' or 6' brush cutter and no cab. You're already feeling the limitations of a standard L when logging. I have no idea what you have that you're calling sugarbush, a quick google shows only a plant native to Arizona and southern California, so I don't know what you want to do with it.
In short, I like the size tractor you have for smaller tasks and landscaping. It is not enough iron(in my opinion), for all of the tasks you seem to have. Something like a Kubota
M7060 or a Case 75C would be ideal for the more demanding tasks. I'd keep the
L3800 as a second tractor/cart hauler/chore tractor.
Having both woods and pasture makes it hard to recommend cab or no cab. Some here have a cab and don't have any issues with getting plenty of timber down. Others have horror stories. Others still will say to put the pasture to work and raise some food!
I think having a tractor at all is a good thing, because even if you get frustrated, have to slow down or take smaller bites at jobs, you're still getting work done. This gives you some breathing room for running the numbers and figuring out how much tractor you need, and if you can afford that size of machine and the implements to go with it.
Just my :twocents: