2. What things should my maintenance man look into for weatherization projects?

Weatherization is such a broad term - however have your home handyaman, condo maintenance man, HOA or Apartment Building maintenance man or maintenance team look into the following:

Door bottom replacement inserts, threshold insert strips, rubber threshold parts, double entry and commercial door weather stripping, astragal pile seals, extra long wool pile seals, window weatherstripping, window replacement parts, seals, weather strip parts, draft excluders, patio door weather stripping, sliding door tracks, sliding door weather-stripping, the gray wool pile seals, On the outside of your structurs inspect all areas where two different building materials meet, including exterior corners, outdoor water faucets, siding and chimney areas, foundation and exterior brick or siding abuttments, cracks and gaps that could cause air leaks at electrical outlets, switch plates, door and window frames, window weather strips, seals, electrical and gas service entrances, baseboards and weather stripping around doors, fireplace dampers, attic hatches, wall or window mounted air conditioners etc.