However, in general it sounds like a typical holdover tenant scenario.

I typically have a cashier's check from the bank with the tenant(s) name on it.

Pest control, this one we typically do a curtesy first treatment and then any subsequent treatment is up to the tenant whether they want to keep the service or do it themselves. 3.

What is the typical payout for PM who manages Section8? 

The column titled "m_nights_altered" in the Airbnb booking sheet typically indicates adjustments made to the original reservation.

The IRS requires the hours to be specifically in real estate trades or businesses, which typically means activities directly related to owning, developing, operating, or managing real estate properties.IRS Publication 925 outlines what counts as real estate trade or business activities, like development, construction, acquisition, management, leasing, and rental operations.

You only need 20% to qualify, along with a credit score typically north of 660.

That should get a response from him (not recommending actually moving it without attorney confirmation but tell him that) - that typically will get a response.

Additionally, there are several DSCR lenders who have various products for this, but most have something similar to Delayed Financing as well as cashout refi's with seasoning typically around 6 months. 

One month of vacancy, other than in egregiously under-rent situations, typically wipes out a year or more of additional "market" rent, so you have to plan accordingly.