It sounds like you’re bringing ample experience to the table, which will definitely help as you start building your portfolio.

I'm planning to start an LLC but I'm wondering if I should wait until I have 100% chosen my market so I use the state of that market? 

The short answer: YES, you usually need to send 1099s if you're a landlord, regardless of the number of units.The confusion comes from the fuzzy definitions of "running a trade or business."

Will definitely pick your brain sometime when we are ready for the next one.

Quote from @River Sava: Hey Carter - With a DSCR loan, refinancing into an LLC is definitely possible, plus these loans don't require a full year of seasoning.

@Shwetha Pindikuri,Assuming an FHA loan with a second mortgage can be tricky, but it’s definitely doable with the right lender.

Definitely a few ways to go about it. 

I’m wondering if $23k of my own liquidated funds is reasonable to start looking for an investment property?

I've been incredibly lucky with tenants, turnover, properties, appreciation, connections etc.That said I do occasionally find myself wondering, what if....If I had bought in Florida or Texas or a booming college town. 

I'm definitely going to look further into all that you mentioned.