If the software is not simplifying your life or making you more accurate, you shouldn't use it.Software does have 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.

I'm not in your market area, but if I was, I would be using you as my top data resource go-to guy. 

I've recently had to switch cleaners and that is costing me an additional $50/stay.

That would be like me posting my rentals on my own website in the hopes that I get more exposure than on Zillow or Apartments.com.Consider it a marketing expense. 

Any insight in this market would be greatly appreciated!

Quote from @Jake Dunsmore: Hey Tony, I am a investment real estate agent here in Kansas City buying/selling off market deals very frequently.

Who's your market? 

I created BrightInvestor and would be happy to chat about how we go beyond just market research but also help you find the properties well - with free owner phone numbers and sales comps. 

I need someone who is motivated to generate direct bookings, especially since my property is themed, and Airbnb doesn't do a great job of marketing the theme. 

You basically outlined your issues and no one can help you with that. 1) The market is the market.