But, I’m geared to Real estate solutions.I would check on the following. 1.  

Nicer areas are going to  be negative Geared so prepare for that..

I want something geared more towards long-term rentals for this side of things, something that makes payments super simple (with a lot of options) for tenants would be great. 

I had a lot of luck with ASI ASI and Safeco early in my journey, and then I stumbled upon a different class of insurance companies that are more geared towards investment properties.My policies are currently underwritten by SES and they have been great to work with and very geared towards the investor.My insurance agent is a sage source of counsel on the subject and I bet he'd be a good resource for you if needed!

I know there are many property management programs available, but I feel these are geared more toward operating the properties rather than tracking a portfolio.  

They also have a much more modern look to the software and they have a good Mobile app geared specifically for tenants.

As a gear head love your analogies!

They are starting passive pockets which appears geared toward passive investments.

In the end the questions were geared towards encouraging me to:  1. eliminate my separate cleaning fee and include it in the nightly price, or 2. lower my cleaning fee to get more bookings. 

@Michael Fucillo haven't played with RentVine also.Would recommend Buildium for what you need as it covers all the basics.Everything else is more geared to managing for others.