These are wood frame Hovnanian units built in 1986 that are holding up well, but windows are starting to fog, HVAC units are coming due for a second time and the kitchens are beginning to show their age.

Loosely read, or common-sense read, replacing windows in no way alters the "structure" so why permit?

Suggestion: Put up blinds of some sort or window coverings.

I know it depends on the number of seams, wall height, amount of doors, windows, etc. but on average, how much caulk would you guestimate a painter would need to paint a 2,000 square foot house?

This is the import slide you want which all respectable importers use at least in my market.I could go on and on but dont settle for some name-less trash just because it is Chinese.  

These differentiators will be the difference between success and failure if/when occupancy slides.

Doors closet windows? 

A razor knife around it cutting the paint and some elbow grease usually get it moving, then address springs or weights on them plus some soap on side helps it slide. 

I have my tenants deposit their payments directly into a special deposit account each month at the bank Drive-through window.

Lawns are mowed, houses are painted, windows are fixed and porches are clean.