By doing this, not only are you increasing the value hopefully building you some equity (giving you some boost in your net worth) but also increase rental potential too. 

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.

Here is a link to all 3 forms you will need: https://www.biggerpockets.com/files/user/ventekrealty/wholesaler-documentsIDEALLY, BUILD A CASH BUYER’S LISTIt’s always best to build a cash buyer’s list BEFORE you start putting properties under contract.

(Insert some sincere rapport-building compliments or questions here - about their yard or dog or whatever.)  

Where we fit into the "turnkey" model is that our marketplace specifically focuses on newly built properties or renovated homes in good markets with property management in place so you are not having to try to self manage from a distance or build a team on your own.

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.

Maybe they’ll build a wall around DC so that he can better control his new Kingdom!  

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. 

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.