Hey everyone,I’m analyzing a potential house hack in Waterford, CT and would love some feedback from the community.This is a unique property because it has two separate single-family homes on one lot.

The simplest business model for a rookie is a single family home. 

It's currently a single family home that was used as a primary residence in the upper level.

I only have a few single family long term rentals so this is a little out of my purview.

I would not consider a duplex multi family although it does have some of the characteristics. 

Quote from @James Wise: Why do we allow people who can't even afford to take care of themselves and their families the opportunity to vote? 

There are great resources and people to help in your journey, Staten Island is great for both flips + buy & hold especially Multi Family.  

You’re moving from single-family to multifamily investing, consider DSCR or commercial loans that qualify based on rental income instead of personal income.

As the first project, I would suggest a small single-family or multifamily property that requires small to medium renovation, and hold it as a rental or flip it on the market.

Where STRs are allowed / zoningSTRs are permitted in single‐family dwelling units within single‐family residential districts or designated single‐family residential areas, with a permit.