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

You are possibly setting yourself up for immediate failure.....there are too many moving parts and too much money involved to mess up this facet of the project.

It sounds like you’re taking all the right steps to set yourself up for success.

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

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

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.

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! 

It certainly sets an interesting precedent as it means if you add a safe unpermitted unit today, it may be protected in the near future so that safe units are not removed from the market.

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. 

I like to set goals for 6 months, 1 year, 3 years, 5 years, and 10 years.