I manage 400 rentals and the most significant claim ever filed was a kitchen fire that cost $20,000.

You'll let them break their lease and hand them cash.I manage 400 rentals.

Could it attract squatters, or is it the right move for responsible property management?

Far more than most real estate acitivies and much quicker think about it.. you sell the same info over and over and get paid instantly you have no roofs to fix no tenants to manage etc etc.. you do have reputation management of course.

Now we are considering creating a Holding LLC that will be managed and owned by both of us.

I'm a broker and property manager here in Sacramento, I manage about 100 investment properties, multifamily LTR and STR. 

( Regarding interior, and not HOA, management, location)Anyone has experience renting for snowbirds?

I am licensed agent but work for an investor doing grounds management.

Start as a co-host and work under a vacation rental management company in the area to learn the ropes.

Managing 17 shopping centers and selecting sites for new developments is no small feat—kudos to you!