I can't re-iterate enough how much better data I have actually spending time analyzing my market and understanding my competition. 

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Our market is extremely competitive for rentals and homes for sale  so I will be putting an ad on Marketplace, seeking an investor to purchase a property and lease to them, as they can pay up to 2500 for a 4 bedroom, and more for higher number of rooms. win/win. 

So as long as you take the time to add your handyman, plumber, electrician, HVAC company, etc into the software it should be as easy as the push of a button when the request comes in. 

The person, not company, you hire for SEO, or any internet marketing program, needs to understand your business operation, geographical area, target market, marketing position, competition md any other relevant information in order to design a program that will work.  

Which means they'd rather wait until there is more competition in the market! 

The Hocking Hills is popular for short term rentals but is competitive.

It's used to determine the cost of producing a product or service, and is a key tool for businesses to remain competitive and profitable.

And the housing market in my state is very competitive and an average house is almost $850K. 

@Andrew Freed is a good person to get in touch with about that as he is a MA multifamily investor who does a lot of meetups.STR is a tough way to start right now because in most markets the table stakes to be competitive are very high.