Losing 60+ % of your population for a city of this size is unprecedented.  

I've found that when I try finding other deal types or other business models or niches, I end up losing a ton of valuable time that goes nowhere. 

I am not going to deep dive here.I usually lose these sorts of deals to people willing to underwrite more aggressively. 

(End)Unfortunately, HOAs are often ran by individuals who are not the most knowledgeable on regulations, accounting practices, and more - and property managers do not want to intervene for fear of losing the contract. 

Reason I ask is in note investing it is actually usually pretty difficult to lose money consistently, thus the questions. 

My experience in a years time clients lose or can't find all the documentation of repairs.

I'm worried about the bank going under and losing my job. 

In some jurisdictions, you are liable for 3 times the value of the property if you lose.

If you have to lose a few hundred a month on a long term tenant, it might be better than selling it.

Very generally speaking the areas of Hartford and New Haven where you can hope to attract qualified tenants (assuming that is your goal) are very expensive because most of the people with something to lose that live in these cities generally live in 2 or 3 areas.