We get inquiries all of the time on Airbnb/VRBO/etc for large group functions at our properties, even if we say in the listing it is not allowed. 

Your GC will know how to apply for the correct permits.Avoiding the issues in the future is a function of respecting the permitting process in the first place.  

@Zach Denny Did you ever put your deal together, if so I'd be curious what the bank required on CLTV and if you had to source the total down payment (PP-First Loan) then apply seller second, or if the bank let you do all that at closing functionally making your DP = PP-First Loan-Second Loan.

Consider using DSCR loans- Cash flow of the property is considered in lieu of your income3.Consider purchasing in a different asset class (Large multifamily) where borrowing will be a function o fthe property income, not yours

Weekends for a lot of people are usually tied up with kids sports, family functions and trips.

If you're looking for software with strong rental accounting capabilities though, there are apps that have this functionality built into them (rather than paying extra through RentRedi to use the REI Hub.

.: An appraiser's word for 7 is functional obsolescence...

Secondly, calendar and email functions/apps on computers and smartphones provide great records and a log.

They have a bigger single family home and a tiny home on the property, but there close proximity and shared driveway present functional problems that are undesirable for guests. 

I find new lending opportunities by networking at local RE Meetups, Training Classes and real estate functions.