Given that the deal is off-market and there might be limited information on pricing, you should compare the property to recent comparable sales in the area (comps) to confirm that the price is fair.

I know the state has CA fair plan insurance for high risk properties and I know its cost.  

I always play by fair housing laws but not giving me a pick in my tenant is not to my liking!

If insurance approves the claim, I figure having the tenants cover the deductible would be fair. 

Borrowers need skin in the game.

FB Marketplace is also fairly easy to use, but depending on your location it can be a waste of time.

I don't think they differentiate the rental type for the writeoffs.I've researched this a fair amount, from what I understand there's an exception section 469 of the tax code that says if you actively manage the str and have an average stay length of 7 days or less then it's treated as an active business and the income is therefore not passive and expenses are able to be written off against W2 income.

I have to ask where you got some of the info in your post because to be fair and accurate if its from a media outlet.  

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.

Hopefully, the landlord and tenants can mutually agree on an early move-out and fair compensation.