I came across some articles stating that these towns plan to regulate the short term rental market.

Income received prior to that date would be considered rental income.Here's a good article on the facts and circumstances that would need to be considered: https://www.jmco.com/articles/real-estate/lease-options-sale...How it is ultimately treated will affect both the buyer and seller.

Lotta easy to find information about this topic from the SEC.    2 SEC Charges in 2012 and 2023.Res Ipsa loquitur-The thing speaks for itself

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

This is the first time I’m seeing someone mention a 2nd position loan, I’ll have to do some more research on that topic.

Sharing an article published just last year on BP on this exact question:Short-Term Rental Loans: What Are the Options and How Do DSCR Loans Stack Up?

Thanks Check out this article on BP published on this exact topic - the "5-10 Unit Multifamily Niche" has some very specific financing options - including, the Multifamily "DSCR Loans" that @Brian Cauldwell mentioned - these look like SFR loans (no tax returns, 30-year fixed, Rent/PITIA to calc DSCR etc.) but are for slightly bigger propertieshttps://www.biggerpockets.com/blog/multifamily-dscr-loans

I've done extensive research on the topic and have the resources to execute, I am looking for advice from someone who has done this before and can assist with the correct steps. 

There are other threads on this topic you should use the search feature to look at them.

They have a real estate specific version and while it's $700 a month + $2k setup fee, it absolutely blows everything else out of the water as it's tailored specifically for real estate agents.Here's an article from realgeek about it: http://www.realgeeks.com/blog/infusionsoft-marketing-real-estate-agents/