Generally the southern US is a great place to invest for me, but I only do multi-tenant retail, good growth, better regulatory environment, great people etc. 

I own 1 profitable rental property and I am retired, keep separate records on my rental property.According to IRS guidance it states:  "If an interest in real estate fails to satisfy all the requirements of the safe harbor, it may still be treated as a trade or business for purposes of the section 199A deduction if it otherwise meets the definition of a trade or business in the section 199A regulations."

Conventional lenders will require 12 months on a cash out refinance while DSCR lenders do not have a seasoning requirement. 

What Erik said, also, you need to be aware of seasoning requirements (with the dscr lender) prior to a cash-out/refi.

Am I still required to send a security deposit statement showing the amount they owe to me? 

Although most hosts don't allow it, they're leaving lots of money on the table.Tread cautiously as this does violate many platform's terms of service.Additional steps are required to protect yourself, which I'll review in the Drawbacks Section of this postGoogle SEODepending on your niche and location, you can rank on Google Search for "rentals in your city".

They're going to require that you file a form with them every single year (it's Form 3840) and on this form you need to report back that you still own the new investment property, and that you haven't sold it and haven't received the income from the sale. 

Negotiate purchase price and financing terms aggressively to secure favorable terms, exploring different financing options like FHA loans, VA loans, or conventional loans with low down payment requirements.

Fannie/ freddie have different guides on this, and i do see different lenders interpret them differently. for example, one requires you to OWN your primary residence in order to use rental income on the subject MF, the other will let you do rental income from your MF subject property with a "present housing expense" (rental housing expense being ok) so long as you have a 1 year + history of landlording (which it sounds like you do). maybe ask your mortgage pro if they are giving you credit for rental income from the subject property units?

The estoppel will probably require you to make contact with these tenants and come up with an end date on the lease.