Like others have said your two most important and fundamental factors will be your handyman and a housekeeper. This can be a challenge though the most important task in pivoting your home to a STR. For one property I'd say you can probably handle the communication and day-to-day logistics on your own though if you continue to expand and add more properties to your portfolio I would definitely suggest a virtual assistant to handle the guest communication.
We always recommend Smartbnb as it helps automate the standard pre-check-in, in-stay, and post-checkout communication.
Every property needs to be re-supplied every 2 to 4 weeks. For that, our favorite method of online shopping is Amazon Prime Now. Different from the regular Amazon Prime, it ships products from the local warehouses and offer delivery in as soon as 1-2 hours
As a whole, a property can take anywhere from 10 to 30 days to properly set up and automate. In part that’s due to the unknown variables, such as how long it will take to find a reliable housekeeper and handyman.
Beyond that, running a property remotely really isn’t that difficult as long as you can find a good housekeeper. Everything else — such as maintenance, pool maintenance, etc. — can easily be arranged remotely. We have properties in 5 cities and do it all remotely this way.
Hope this helps!