Do you like cherry pie? I would suggest planting a good pie cherry like Montmorency, very commonly sold. In the stores and at the markets it seems like you can buy sweet cherries by the bushel load but not sour cherries/pie cherries. Also good for jam. That's what I would plant. But I love cherry pie and jam and would freeze some or can some for future use, so getting a tree would be a way for me to have a product that is hard to find otherwise.

Same goes for apples, I'd plant something that isn't a dime a dozen in the stores. Don't know what the self polinating apples are. If you would go with two, I would use a Dolgo crab for the pollinator. Crab apples make wicked good applesauce, and I've eaten Dolgo, they are sweet for a crab. Will pollinate any other tree so then you can take your pick. Otherwise, Google self-polinating apples to see what your options are. You can get a couple kinds grafted onto one tree, but I dunno, seems kinda weird to me but what do I know, I grow crabs.

My favorite apple is Empire. I've had good luck growing Cortlands. Both of those are very common though. My mom fondly remembers Northern Spy growing up. That's less common and I have no experience with it. Another one I might grow, just for the name, is Winesap. Also depends on if you want a pie apple, a canning apple, a storage apple or an eating apple. That's why I like Empires, they are good for sauce, pies and eating out of hand. Don't know about them for storage though. I've never grown an Empire apple either.