@Jonathan Buelow My accountant and bookkeeper could care less about what I set my rents at.

You should really do the research to understand your market before you can trust a software to appropriately set rates for you.  

If you have a plan A and a plan B going in you are setting yourself up to fail right away because you have told your minds already it won't work so you won't put your all into plan A.

Approaching it like that would also automatically set an expectation for the owner to pay maintenance expenses. 

You cannot beat the power of an ADU for peace of mind, leveraging your home to pay less monthly and reduce your expenses and give you the experience and confidence of doing constriction, getting permits and working with the city and managing a very easy rental.

Then refinance it in 12 -24 months to take cash out and convert to a full time investment.The other property I would find a Duplex or 3-4 unit in or around Crystal River and set it up as a STR. 

It is a lot of work and I understand you want to "pour some gas on the fire" but likely you will just be setting cash on fire.Good to know thank you! 

I tried to set up quickbooks online, but without paying $720 a year for the ability to do class tracking, it seems like it wouldn't be as beneficial.I know there are other tools out there more geared towards real estate like xero, etc, but I'm still trying to avoid paying so much every month.Has anybody used realtyzam or rentalhero (rentalhero.io) they seem to be linked? 

Whereas the majority of the existing clients have stayed with you, but the whale client is with the ex-partner leads me to believe that if this heads to any type of judicial setting that no damages would be awarded.

When the transaction closes, the purchase is funded, and we set aside additional funds in an escrow account to pay predetermined professionals to make any required or desired repairs or upgrades to a property AFTER the buyers settle on the purchase transaction.