There should never be surprises before you close, during the course of the loan, or even if you need an extension.

If we do decide to do the longer stay:1. do we proceed through Airbnb for booking or set up a secure way to collect rent payments?

It is suggested that  "Small" landlords use a collection agency, who will report the non-paying tenants to the credit bureaus.   

If that's in the stock market, financial experts say that to be $500/mo.Stock market of course is liquid but I'll keep multiple six figs liquid just for safety.In a recession I'd sleep much better at night collecting monthly rent rather than have terrors about the stock market.

Some tasks, like leasing, require more upfront time, while others, like rent collection, are ongoing but minimal if everything runs smoothly.

I owned a condo that flooded and the offices below suffered extensive damage.  

I have seen Section 8 "gurus" who boast about collection all of their rent money like clockwork from the government every month. 

We are on the month-to-month lease now as the automatic extension of the original lease. 

This is the exact reason why you never collect just one month rent as a security deposit.

I assume it will spend zero the last few months while collecting 100’s of thousands.