The expert you are looking for is called a Land Surveyor, they're going to want 5k-15k, if you want to make any money on your project you need to build a house so you also need an architect, they will want 10k-50k, if you're in a hillside zone you will also need a geologist, they're going to want 10k, you will also need a biologist, they're going to want 2k-5k.

Quote from @Mark Sullivan: Quote from @Tim Delaney: One missing piece of info here is how much cash you have available to invest at the moment.My initial thought was sell LLC B and hopefully you have a few hundred thousand available on top of that to buy the new building.

Since they are responsible for maintaining the relationship with you after the transaction closes, this approach adds an extra layer of confidence and security to your investment.If you can't find an investor agent that you like or trust that is also a Property Manager or works under a brokerage that has a Property Management Division, I would ask the agent if they recommend a Property Management Company.

In Reno and metro areas, insurance companies primarily focus on roofs, the age of the building, wiring updates, and water pipes, as mentioned @Cameron Moore.

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.

If you're confident you can find better cash-flowing deals or scale your portfolio with leverage, it could make more sense to reinvest rather than pay off the loan.

The ultimate guide to building rapport and great 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. 

Build your knowledge with books, podcasts, and online resources, and network through local REIA meetings and virtual platforms.

Bonus Tip: If this quadruplex is out of state, I’d highly recommend building a reliable local team (cleaners, handymen, etc.) and maybe consider hiring a co-host or VA to help with day-to-day tasks, especially if you scale up.