I'm thinking of the vacuum hose setup that hooks to the skimmer. Should be able to hook it as you would for vacuuming but set the valve to waste and leave the hose in the deep end of the pool.

The plastic sheet will float. Just start filling on top and let it sink as you suck out the bottom. Shape of the pool shouldn't matter as long as the sheets cover the pool with enough overlap to account for dropping down as you fill.
Hope this answers your questions...if not...ask again.
Al