I just can't accept such a constant ever increasing loss, even if I can afford it. 

. - In the event that you do get a deal, that you do not violate the intent or letter of an increasing number of anti-wholesaling laws, and that you actually receive an assignment fee, you will walk away thinking that your role is over.

Depreciation recapture applies at ordinary income rates capped at 25%, increasing your tax liability.

In California, this transfer could also trigger property tax reassessment, increasing the tax bill.

Or is it calculated daily and the base rent increases after 10 days when the late fee hits the account?

So spending 200k on an ADU will likely not increase your property value by 200k. 

Currently we are seeing STR owners posting for sale due to reduction in prices they can get per night and the vacancy rate increasing. 

While the vetting of residents is greater with FF over an Airbnb or similar platform, I think Airbnb overcharges for the increased convenience. 

If you have access to some money you can increase your equity in one jump.

But in smart buying, if someone has enough cash to pay cash for a property, they could easily stash a good chunk of that away to cover downed months and still leverage to increase the overall returns on their portfolio.