For five acres either a subcompact or compact tractor will serve. 4-WD should provide traction on your sloped land with R4/industrial tires.
Have you performed your own service on your L&G Tractor? If so, you can perform routine service on either a subcompact or compact tractor.
Subcompact tractors with a Mid Mount Mower have about 3" or ground clearance with mower attached, 9" ground clearance with mower removed. Removing and replacing MMM is easier than in the past but still not fun. Minimal 9" ground clearance can make working in woodland difficult. Subcompacts have two-range (2) HST transmissions. Subcompacts generally draw 48" wide implements.
Compact tractors of 1,600 - 1,800 pounds bare tractor weight have larger wheels and tires. Larger wheels yield greater ground clearance, usually at least 12", and a much smoother ride over rough ground. Compact tractors have greater FEL lift capacity than Subcompacts and usually have three-range (3) HST transmissions. Compact tractors generally draw 54" or 60" implements. Allowing for a 5" overlap in use, a considerable improvement over 48" implements.
Either a subcompact or compact tractor will operate a MMM equally well. The longer wheelbase compact will be a smidgeon less maneuverable.
If you can afford a 1,600 - 1,800 pound Compact, go for it. If you consider Kubota, focus on the
B2650.
When considering a tractor purchase, bare tractor weight first, tractor horsepower second and (narrowly) rear wheel and Three Point Hitch
ballast third.
The MMM is a inferior mowing option IMO. MMMs cost close to a used ZTR and get in the way of doing anything else. The loader also gets in the way of mowing.
I too recommend a Zero Turn Mower for lawn mowing. Or keep your L&G tractor and skip new tractor MMM. Instead, acquire a Bush Hog with your new tractor for trails and your meadow.
VIDEO: Kubota BX Series VS. B Series - YouTube