Winesap is a tart/sweet heirloom variety that dates to the early 1800's. Good flavor, we've used them for pies, butters, dehydrated, applesauce, and cakes. Here is a quote from one site describing the flavor: "Winesap apples have a sweet, fruity, and spice-like aroma and a balanced, sweet-tart flavor with tangy, sweet, and subtly savory wine-like nuances."
They've got a fairly thick, tough skin but I don't peel them before eating fresh. Crisp, non mealy texture, they are sid to be a decent storage apple although I don't try other than keeping some in the fridge. Historically, they were used a lot as the base apple for ciders. They are one of the latest maturing apples and it can be well into October for maturity some years.
Don't know if they would survive in your area Matt, they are a zone 5-8 apple.
Growing apples is not difficult, but can require a lot of insecticide sprays if you want really nice looking ones. They should be pruned every year in late winter, but pruning my two semi dwarf trees takes about 1 hour annually. Pears are about the same as apples in regards to care, annual pruning and insecticide sprays periodically.
Cherry trees (sour) need annual pruning, but a lot less sprays.
Bottom line on fruit trees is all of them will need annual pruning, but that is no big deal. From there, it's up to you how much you want to spray or monitor for insect pests. Some won't spray at all. Some will spray every week or ten days, which I think is way overkill unless you have an orchard that is selling to the public.
Unless you have a lot of space, I'd recommend dwarf rootstock on fruit trees. Even a semi dwarf tree can overwhelm small areas. I buy mostly bare root trees in the spring which will generally be 3-5' tall.
Time from planting to fruit production varies and is generally quicker for dwarf than semi dwarf. Apples 4-5 years, pears 5-7 years, cherry and plum 3-5 years. The time will also vary somewhat depending on variety.