$550,000 on main home - Deductible on Schedule A, but see third point for limitations.

$150,0000 on home that is now a rental - Fully deductible on Schedule E.

$300,000 on second home - Deducible on Schedule A, but because this was after change, you are limited to $750,000 between this one and the Main Home (fully use the higher interest one, and use the lower interest one for the rest).

$150,000 used to improve rental - Fully deductible on Schedule E.