Ryan, My suggestion. Write down every single operation you have at your place, and what piece of equipment you use or need to perform the job.
Plowing an acre and brush hogging 5, hauling your syrup wagon, and most of the things you list, there is no reason to sell what you have, an 8N is fine for most of that.
Lifting logs and things like that, you may find a backhoe or skidsteer fits the bill. To me a skidsteer is more handy and you'll do things you never imagined, and do them a lot faster. Plus for oddball jobs you can rent the attachment you need.
I ended up putting a quick-attach on my 50hp tractor loader, I now can do just about any chore I need with the one tractor.
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