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. 

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.

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

I am wanting a LLC for protection as well creating it separate from myself I would like to be able to build business credit and not have any based on my personal credit and I understand there is some tax savings using an LLC

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.

you have to inspect BEFORE the sale. 

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. 

So any extra pointers or tips , books, would be great guys I would love to connect and build relationships!

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.