I don't see that there should be any disclosure requirements for someone who isn't licensed since the rules for that are specific to licensees.

For those who have flipped houses in multiple cities across Texas or Florida, which ones stand out as being on either end of the spectrum in terms of how difficult and time-consuming the permitting process is? Are the...

A lot of clients set up rental properties with DSCR loans which requires less paperwork.

I contacted a title company to officially record the sale, but they are requiring 3 separate closings (and tons of extra fees) because there will be 3 liens/private mortgages recorded (one is the original mortgage that I want to reassign since the interest rate was very low; the second will be held by my son to my daughter for his portion of the equity in the home; and the third is the difference which will be between my daughter and my other LLC). 

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."

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".

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? 

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.