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.

One bad tenant can lose you several good ones if not dealt with.My leases are written in common language.

DM me so I don't lose you, we are not based there (CO-based until probably 2033)

The Jade District has great public transit and biking access, but with the proximity to 205, the neighborhood can appeal car commuters, and I wouldn't want to lose them from the outset. 

That's fewer individuals than active players on NFL rosters.

How much money can you afford to lose? 

@Hector Haro there's no helping someone who pinches pennies while losing dollars.