Google MapsGoogle Maps is a fantastic and free tool for scouting potential properties and understanding neighborhood dynamics.

In our property, the house was open to the air in the damp environment of coastal Florida, no heat or A/C at the house.  

I live in Fairfield County and am looking to invest in a property for house hacking somewhere in New Haven County. 

I think he already has a property in mind.

I understand federally I can deduct payments on mortgage interest, property management fees to my onsite property manager, maintenance, etc.

Yes, you spent time to acquire and manage the property (unless the cash flow can also support paying for a good property manager), but you have none of your own funds invested, and you can use those funds for something else.You ARE recouping your initial funds.  

This property will require about 45% down to hit the 1.25 DSCR that is the median requirement for a commercial real estate loan.If you want to be at that price point with that much for the downstroke, you need to be looking at higher risk properties with a higher cap rate.

I had a W2 I wanted to leave and thought that owning 30 rental properties would be enough to retire from corporate life.

I want to understand how many properties are bid on by third parties and how many revert to lenders.

My husband and I are still working our W-2s (and extra), but we can't move on another property until this one is at least paying for itself.