As properties age and neighborhoods shift what was once a A class property becomes a B, then a C becoming more affordable over time.One resource that you should look at is "The Section 8 Bible" in some ways this is a book on how NOT to do things but there are some truths in the book as well.  

And once this kind of behavior goes in, the right and most humane thing to do is make it very clear to the tenant in a lasting way that this sort of behavior is not permissible from adults in our society who have signed a contract with each other, because it isn't.Yes MA is a tenant-friendly state.

Regardless of the “right time” I am trying to shift to seeing value where others don’t.

(get rid of it meaning sell, do other strategies so you don't loose much $)Advice, shift your mindset of making $25 less today vs what can you do tomorrow. 

and I had some help recently from my girls:The soup, crescent rolls, and make-shift table I used from the countertop drop out (cut for the sink) made this experience much warmer for me! 

I actually think STR is the way our society is going.

None of these shifts will happen quickly but they will add up fast.

My experience is that the luxury student housing boom in Columbia has shifted this market in two important ways.1) Parents and students expect to pay high rents.

Our clients having the most success now are shifting their paradigms. 

Timing the market is literally impossible- there's a great allegory about that in "Shift" by Gary Keller about how it's impossible to time the market and taking action is so much more valuable.