Hi Matt,I'm in a similar situation as you were and wondering how this strategy worked for you or if you found any better ways to organize the finances for the house hack without the rent covering the mortgage?

Yes, I live in Boquete Panama and I own a small organic coffee farm so I know that business too. 

Once you have a shortlist, sign up for an account with each one and test them extensively to see how they function.

In my experience the basics for a functional RE based CRM are:Custom Fields for Data Objects (Leads, Prospects, Applications, Buildings, Units, etc...)A Screening Engine (background/credit checks, employment verification, etc)Online Rental Application (this should automatically run the application through screening)Ability to mass email/sms leads and tenants to provide informationSurveys/Inspection formsI've been building real estate CRM tools for years.

Toledo REIA and PIN (Toledo Property Investors Network) are both professional organizations that might help further your education and networking locally.

These are just very different functions.

We built out our own portal and accounting database for that functionality because we were not finding good software that could handle a higher volume of receipts AND tie it in with the rental property accounting. 

I could save a whole lot of cash mowing my own grass, ironing my shirts, painting the kitchen, organizing my garage, and changing my own oil.

Want to know if this organization is what it advertised to be.

I BRRRR several properties in the past but wasn't very organized.