I am looking to purchase my first real estate deal.

I recommend that you stay on the safe side and do send 1099s to your wholesalers.You do not need to send 1099-NEC in these cases:You paid the contractor electronically (more on this below)You paid the person a total of less than $600 during 2023Payments for purchasing all kinds of goods, materials, and property, including real estate itselfThe person who worked for you is a corporation, and you made payments to his corporation.

A JV structure is good for a one-off deal because the only commitment you have is to the investor(s) and that individual project or deal.So in part, the answer to your question depends on what your objective is. 

Purchase price: $57,500 Cash invested: $100 Sale price: $90,000 Small vacant lot, overlooking I-40 on the westside of Nashville How did you find this deal and how did you negotiate it?

@Colin Fordcongrats on your purchase in RI. 

I am wanting to make sure I will be working with a title company that is familiar with wholesale assignment contracts, seller financing, lease with an option to purchase and possibly sandwich leasees with an option to purchase.

That should be your focus, not how to purchase the land.  

I have construction loan on the current house I'm building and used similar strategy (land was purchased outright and used to cover majority of the down payment).

House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

In the case of the OP, he believes prop taxes are too high, tenants are crazy high risk, STR is too much work, does not want to purchase more.