In addition to STR'ing the main house, he is building 2 more units (ADUs) on the back side of the property.

@Josh Feit Sounds like this is a Class C building in a Class C area.So, how is your advertising geared towards attracting Class C tenants?

Since I work full-time, my near term focus is building my property portfolio and maximizing the tax benefit. 

The liability coverage is way better, the building coverage is often better, and commercial policies typically cover loss of business income as well, which a homeowners policy isn't going to help you with.California + wildfire area + STR is super tough. 

My goals are to start building an investment portfolio of professionally managed (I could tell you all the reasons I will not do it myself) multi-family properties and, in time, develop a property in the Northwoods (Wisconsin/UP).

To invest out of state successfully, focus on building a strong local team (agent, PM, contractors), automating deal analysis, and using contingencies to protect yourself.

Since you're open to markets beyond NYC, you might want to connect with local investor meetups or REI groups in those areas to build relationships with agents, wholesalers, and lenders who understand the nuances of each market.If you're looking to break out of analysis paralysis, maybe start by narrowing down one or two target markets and running numbers on actual deals.

We are building a place with HELOCs then after it is built we will finance it and pay off our HELOC, at least thats our plan. 

Just want to mention that sometimes it works out better to raze an existing property down to like 2 studs and rebuild around it so that it still is classified as a remodel versus a complete new build. 

Mine is a 2022 build  Hey Ryan, Your property checks alot of boxes for me for a MTR focused on attracting families as a whole home rental.Single story, Good school district, Little to no competition on Airbnb, No HOA.I bought a property once in 2015 and it barely cash flowed as a LTR but now 10 years later, I cash flow as a LTR about $600 per month.