water infiltration into crawlspace + insulation below first floor

[Peter Graves]

HI BP, I'm looking for a contractor to help us solve water infiltration issues in our unfinished crawl space. Also, we need to install insulation below the first floor due to previous tenants saying that the floors are too cold, and heating bill too high. The building is a 1900's  3 flat located in Chicago north side. Any advice or contractor recommendations would be very much appreciated!