I had a tenant do the same last year.

What are your investment goals? 

@Casey Graham 1) Your #1 goal with tenants is consistently, smooth cashflow.

So depending on what your investment goals are and what type of properties (Class A through C/D) and where in the city you want to buy, that can directly impact the level of stability one can find within the market here. 

I have been in the STR market for the last 13 years.

It took us a couple of weeks but we slowly increased their rankings unit they were on page 1 (based on search parameters of course) and they got a 10 day booking soon thereafter.We use Price Labs to check out the date of the last booking.

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.

No evictions within the last year.b.

These qualities are far more valuable than the numbers in your bank account.7.Set clear goals.

Once you have your strategy/goals, begin underwriting as many opportunities as you see in that realm.