Got an automated voice mailbox and the mailbox is full.

For instance I had a special case where I billed the tenant an extra expense monthly on top of the automated rent collection, so I add it as an expense and it would automatically email them and notify me when it was late of course.

10% is probably a little steep, and like John said, a flat fee may be more reasonable.Setting up a proper STR is not cheap, but once you are set up properly, you deal with routine breakage.I recommend managing yourself and saving the 20% personally, getting a rockstar cleaning team and a reliable handy person, using something like Hospitable that can help automate messaging when listing, and reading the book from the bookstore here called Short-Term Rental, Long-Term Wealth.

I'm not aware of software that automates this since a lot of the numbers being input are assumptions made by the analyzer.I will tell you you can dial in your processes around analyzing deals and hire someone to run your processes within your buy box.

But I remember when they weren't so automated and you could actually call someone to talk through issues. 

We shopped for properties based on that and it has paid off.Guest Experience: Similar to what others have said, have good detailed automated messages for guests and a guidebook, nothing they hate more than getting to a property and being confused about how to get in, where to find things, etc.

I use tenantbackgroundsearch.com, although many of the vendors provide automated reports that are nearly identical. 

The PM should have it set up so it is all automated and other than checking rent is paid as are bills, there isn't too much to it and one person usually handles their accounting.

I found someone local who is willing to handle property management (for 20%), but it feels like a waste if I'm already handling the listings and automation and integrations to run the business.

First of all - most people (including real estate investors) are lazy and will always gravitate towards promises of quick returns / passive income promises.But also - what you are describing is something that AirDNA does extremely well and automated - it can be a little pricy, but way way more effective and accurate to do this with that tool - highly recommended