The difficulty is figuring out how to unlock these deals, how to find them, how to communicate properly with a homeowner, etc..

For the most part, my cabin guests communicate a bit (or not at all) and are low maintenance. 

Keep blaming it on communication with the banks.

So good communication and a little bit of freedom on the paint?

My tenants primarily communicate via the latter methods.

If not, you would need to account for that.STR Insurance - You're likely looking at $200-250/mo if you wanted STR-focused insurance with proper liability protection.Virtual Assistant — it’s not a big issue with 1 property, but if you decide to get multiple, you'll find that it’s more work to communicate with guests and such than it is with long-term rentals.

We pull our reports or data directly from the PM software.I agree the reporting and communication needs some work on it.

Yet we have open and clear communication.   

Both of those are 100% my fault for not clearly communicating what I wanted (after all, contractors can't read our minds).

. ;-) What we have here is a failure to communicate.