Andy Sirkin, based in San Francisco but supposedly has done some in Las Angeles. 

Position these as limited-time deals to attract budget-conscious travelers.Be Responsive and Personable: Guests often book based on their interaction with a host.

Sounds like you are going with a Fannie/Freddie type loan based on the cap of 2%.  

If these continual expenses are not made  you end up with slum properties renting for a minimum weekly rate to transients.I don’t know your properties so I can’t form a specific opinion; however, based on the information you’ve shared I trust your opinion and knowledge.  

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

I am local to Los Angeles - based in Orange County.A bit about me: I’m a civil engineer by profession with experience in local government.

ABL, which is the basis for HML/fix and flip lending, will have different criteria and different focuses than multi-year loans based on cashflow and borrower credit score (long term mortgages).

The tenant base, on average, tends to be rougher on the properties, moves more frequently, and cannot absorb any rent increases.  

Also , I would love to connect with any agents who specialize in STR market in Boston Mass area. airdna is pretty accurate . lenders use it to assess rental comps for short terms rentals when financing a short term rental  I use it for DSCR loans as well; it is accurate yet conservative because it gives you the median 50 percentile for the area based on comps.

Every market will have a data center, not sure how this will deviate from the curve of market-based anticipation.