Almost all reputable property management firms have strong indemnification and hold harmless clauses as part of their management agreement.

@Dulce DavisSome private firms would consider blankets but they are gonna cost 2x traditional financingI would take the one with no mortgage and leverage that to buy another and keep doing that - also once in a while may consider selling some inventory to get more cash

With those stats, you'll pull half the accountants in the forum out of the woodwork, most of us would be more than happy to work with someone in your financial position as it means we can provide a fair amount of value.Whoever you work with, I would recommend you consider finding a firm with substantial experience to offer in both real estate, and estate/gift planning given your goals.. 

Can second home be operated by a management firm that has control over occupancy?

a local marketing guru who would frequently meet with us to discuss various business strategies to help grow our detail company heard about the offer. at the time he found out about it the current carwash owners had all but signed an LOI with an out of state private equity firm but were willing to sit down with us and hear our offer!

Just because something worked for one host, doesn't mean it'll work for you since each market is different.

Another thing to know is you will have to create a new listing once the original host takes theirs down.

Just get a firm exit strategy in place (and a backup) for financing before you take action - most cashout refi products have seasoning requirements these days. 

As an Airbnb Superhost for several properties, there could be a number of things wrong here:1) Like @Collin H. mentioned above, there could be a housekeeping miscommunication problem2) If there are holes in the wall, cameras all over the place (inside and outside), etc..then this could also be a host problem. 

I do have the benefit own owning a IT consulting/software development firm with resources I can leverage.