Anyone have insight into the process and timeline?  

This document helps you find the right local broker partner https://docs.google.com/document/d/1YRwDmuSRS6xMCMgD1CpNQjqT...You could also hire a consultant to help you complete due diligence on your property to help you identify the highest and best use of the property.

An opportunity came up quick and now I'm worried how long the process could take to set up. 

If you want to hire somebody for that, I have a girl who can do it for you...You should ask if they're using WordPress to build the website and if they build it responsive (mobile and tablet friendly).Also, if they can create a few pages and install some plugins for you, would be ideal!

The first time they try a charge back on any one of those apps will be the beginning of their eviction process.

To increase the profit margin you may also want to consider hiring out some of the work to speed up the time it takes you to complete the project.

Other tenants were responsible to mowing, some hired it out other cut the lawn them self. 

I’m in the process of finishing the basement and adding an additional 2 bedrooms and 1 bathroom.

Negatives: 1) First time sign up process could be cumbersome 2) Claim processing is temperamental they process claims within a few days but recently they have been taking very long like 3-4 weeks 3) Not all renters get approved and Rhino does not provide a reason for denial.

I'd greatly appreciate any recommendations or suggestions on how i could go about this process differently.