What is your total acreage? You have referenced pieces but not total acreage.
As I read your opening post, you have five (5) open acres. What is the rest?
The fundamental importance of TRACTOR WEIGHT eludes many tractor shoppers. Tractor weight is more important identifying compact tractor capability than tractor horsepower.
The most efficient way to shop for tractors is to first identify potential tractor applications, then, through consulataton, establish bare tractor weight necessary to safely accomplish your applications. Tractor dealers, experienced tractor owners and TractorByNet.com are sources for weight recommendations.
Bare tractor weight is a fundamental tractor specification easily found in sales brochures and web sites, readily comparable across tractor brands and tractor models, new and used. Shop your weight range within tractor brands. Budget will eliminate some choices. Collect a dealer brochure for each tractor model in your weight range.
To cut through clutter I spreadsheet tractor and implement specs. I have a column for cost per pound.
Selling a used tractor is easy. Selling multiple light implements in order to buy heavier, wider implements for a new, heavier tractor requires a lot of time. Depreciation on implements is worse than depreciation on a tractor.
A quality dealer, reasonably close, available for coaching, is important for tractor neophytes. Most new tractors are delivered with a glitch or two requiring correction. My kubota dealer is six miles away. I feel my local dealer continues to add value to my equipment after seven years. Dealer proximity is less important for those experienced with tractors and qualified to perform their own maintenance.
Tractors are inherently unstable operating on sloped ground. Tractor rear wheel/tire spread, sometimes adjustable, is a critical factor increasing compact tractor stability working sloped or uneven ground. A 6" to 10" wider rear axle substantially decreases tractor rollover potential. Larger wheels and tires yield more tractive power pulling ground contact implements and logs, pushing a loader bucket into dirt and pushing snow. Larger wheels and tires permit heavier tractors to bridge holes, ruts and tree debris with less operator perturbation.
When considering a tractor purchase, bare tractor weight first, tractor horsepower second, rear axle width third, rear wheel/tire ballast fourth.