For complicated tracking and scheduling I use Trello.

the hand offs are annoying since if your situation is more complicated, as investors tend to be, you have to explain your file all over again.Separate from banks, non-bank lenders (separate from mortgage brokers), really have more flexibility than a bank due to the regulations imposed after the 2008 crash.

Then there were complications, and setbacks, and town/permit issues, and contractor issues and Covid and so on.

New construction, larger additions, challenging permit submission documents, complicated architectural work.

I spoke with the founder of AirDNA and he said Revenue potential uses a complicated algorithm that says "what days were available, how many days was it booked, how many days was it unavailable, how much does it make compared to comps, and what would it bring it if it was available for the days the property was blocked." 

I have a finance background, so I am certain that I'm just over complicating this.

A lot of 30 year fixed type loans that go on the secondary market will either require 6 months of ownership or it will be a more complicated underwriting process.  

This is a complicated situation.

There are other complications but that is the simplest way to put it. 

There is less risk and complication involved and it is probably easier to cash flow on a conventional loan than a commercial loan.