No matter how good your cleaners and handyman are, something may be missed.

I have a property manager who helps with the booking and renter issues (if any), a cleaner who turns over the property.

You may thing you're buying a vacant lot, but it has $100,000 worth of junk to haul off, or that faded letter on the window when you get up close and personal says "dry cleaner". 

Also, if i reply to a series of text messages (with my cleaner, for example) can I log those as 1 minute each to read/reply?

He really helped me get started. you can easily do this on your own, but i highly recommend getting a cleaner. you can automate messeneging, pricing, and checkin/out process.

I'd think if you had a cleaner come in to handle that aspect and then used an app to manage the leases and things you'd be in pretty good shape.  

I have specific credit cards set up for my cleaners, handymen, etc. so when I see a charge come through for that card I know exactly what it's for and what property it's associated with.

I usually tell them that the process is similar to booking a vacation rental that happens site unseen but if they insist I’ll schedule a walkthrough with my cleaner.

I simply rely on Airbnb and VRBO (although the vast majority of my bookings come via Airbnb).I have a great cleaner and I'll have a handyman, plumber, etc. come to the house when needed for those things. 

In the first call they disconnected my old PMS before setting up any of the messaging, notifications to cleaners, or locks before the end of the call.