We have a pool. The insurance requires at least a 4ft. barrier around it with a locked way in. Our rate is the same with or without it. It's winterized the week after labor day. You never drain pool with a vinyl lining unless you are changing the lining. Vinyl will shrink in sunlight in just a few hours if no water weight is in it. DH shocks the water, covers it for the winter. It's nice and clear when he uncovers it for the summer. A pool takes time to keep up so unless you have a pool service be prepared to have to maintain it several times a week, or more if it rains a lot.