Red Windsor is one of the easiest and most reliable of all apple varieties.
It is self-fertile, so there is no need to worry about pollination partners. It grows naturally in a neat and tidy fashion, and crops heavily. The apples can be picked over several weeks so you don't have to deal with a glut. It seems untroubled by the usual diseases of apples, and the blossom also has some resistance to frost.
Pick Mid-September. Self fertile.