Currently rented for $1800/mo.

About 16 years ago we rented a place in Destin and it had glass top dining table and glass top coffee table. 

And do they care if I do rent by the room strategies?

DSCR loans are based off of down payment, credit score and either actual or market rents so it helps to supercharge an investor's real estate goals and net worth.

I can help you with accurate rent expectations.

You're going to have to scrap like crazy to break even - think rent by the room, short term, mid term strategies that require more work.

The tenant base, on average, tends to be rougher on the properties, moves more frequently, and cannot absorb any rent increases.  

Check with your QI about both scenarios.I did have a client do a 1031, rent it out for two years and then moved in at the advisement of their CPA.  

In NY tenants have to give 30 days notice before they move out to give me time to rent out the apartment again.

If this property is hard to rent, or is functionally obsolescent (only 1 bathroom, no yard, etc), or has deferred maintenance that will be costly, or is in a location that is not appealing to Tenants, then maybe a sale would be a good option in favor of a property that has better Tenant appeal, which will likely increase rent and avoid long vacancies in between Tenants.An option to consider....