They often have rents below market so that their tenants will not complain about a broken furnace that does not get repaired or having to run an extension cord to the refrigerator because the circuit needs to be replaced but the panel is so old the circuit cannot be replaced. 

I'd suspect that the first time the debt service isn't coming like clockwork OR if the bank becomes financially strained, they'll be less lenient on these personal loan --> entity ownership sidesteps than they currently are in the "era of untouchable bull runs".

Our historic overlay requires historic, single pane, wooden windows; however, they’re horrible for utilities.

@Jason Strain thank you for the suggestion!

@Patrick Strain that’s exactly what I was thinking.

Triple pane glass in any unavoidable window.

How many panes? 

First of all, your situation has been a strain on you and your family.

I like her as a tenant, and she really likes her apartment and the location -- she's retired and says she would like to stay for many years.In a recent conversation, she mentioned that the old single-pane windows and doors are drafty in the winter (not uninhabitable, just drafty). 

That seems to me like it would be a lot of strain on the pump but I have never purchased a home on a well before.