Thinking about growing a "good" Apple tree in MA

My mother has a pear tree that gets almost no pears some years, but this year it has hundreds. Its an old tree so the pears are huge. Just what you'd like, if you liked pears. I, however, do not like pears.

I've often thought off and on about growing an apple tree in my yard, but in the end I always chicken out because I don't want to constantly be picking up fallen, rotten apples. But I'm looking at all the pears we're giving away this year and I'm thinking, maybe thats not so bad of a price to pay to get tons of nice apples like Macs apples that I can eat all fall.

There are plenty of apple farms around the extended greater Boston area, so I know the trees are fine with the climate.
One thing I'm a little concerned about is the soil. I put down lawn fertilizer and triazicyde (sp?) three times a year. Not only that, but the previous owners had a pool back there, so would have been lots of pool chemicals in the lawn 15+ years ago. Also, while now it looks like a beautiful green lawn, thats because I buried lots of uncomplicated rough-fill asphalt that they originally used to level out the yard. Plus they were scum bags so who knows what else they might have dumped in the yard. So is soil quality an issue? Should I be getting it tested somehow before I start eating food that I grow out of that soil? Or is that not really an issue?

Beyond that, I guess I just want to know anything people can tell me that already grow trees like this. Any quirks? Any problems you run in to? Anything unexpected? Some trees like sun but not too much sun. I have a very sunny area of my yard, and another less sunny area where there is some shade from some other trees.

Also it's N.E. so the soil is always rocky to begin with. But my whole back yard appears to be made from a large pile of concrete and rocks and fill dirt, with a layer of better dirt on top. I really don't know what lurks under my top layer, besides the asphalt and gravel where the pool was. I have trees growing out of the edges of my yard, so I guess the soil makeup can't be that bad.

Anyway I'm getting lost in the weeds here. Just let me know your experience if you grow a good apple tree that produces apples you actually eat please!

Also I am aware that I can't grow the tree I want from an apple I like. I'd be mcintosh seedlings online somewhere.