I have a list of about 20 properties from him, I just don't know how to start to the assessing process.  

I’d reach out to your attorney asap to get the process started.

But consulting with the town would be good to try to understand what they're permitting process is like.

Lenders desperately need/want business especially in this interest rate environment (right now, the main source of mortgage loan business in Florida is rehab financing as a result of the hurricane damages) and one way the big players differentiate themselves is by streamlining the process.

DSCR loans underwrite to the income of the property, and do not require your personal income, taxes, debt-to-income ratio, etc.Of the 1,100+ loans that our team closed last year, I want to say that only 1% to 2% of those were closed in a borrower's personal name.So, it is pretty irregular for us to process an investment property loan under a personal name.Clients usually opt for closing in their personal name if they simply do not have an LLC established yet. 

However, we will likely need a property manager to assist with some facets of running this rental (since we would not live locally) and would primarily market it through platforms such as Airbnb and VRBO to start, (eventually setting up a direct booking process).Here's our question for those who have experience in STR's or who might be involved in a similar scenario: How challenging is it to meet the material participation hours needed to achieve active status?

In fact, I would estimate that it is mostly upper middle-class folks that have the money and wherewithal to go through the vacation rental process - prepayment of substantial monies, etc.If you only have one property, I would just stick with Venmo, CashApp, or Paypal.

I’m passionate about learning and improving my process to provide real value to investors, whether you’re focused on fix-and-flip, buy-and-hold, or any other strategy.Looking forward to your thoughts and insights!

Do they have to go through eviction processes as well? 

Depending on the volume you would be submitting, find a company that does not have high monthly minimums and can walk you through the process if this is your first time using.