You will need to compare your unit to the competition.

I would consider the cost of extracting your equity from the FL property by sale and then compare that to pulling equity by way of a cashout refinance.

Then compare that to median sales prices in a given zip code.

Instead, I'd just rely on a CMA (comparative market analysis) of renovated properties in the area from your realtor unless you have local MLS access yourself to run the report. 

Given that your property has been subdivided into two rental units, it should indeed be compared to other multifamily properties in the area, not single-family homes.

I just do not want to take this possibility off the table if it could help us really get moving in terms of number of doors we have rented out (a 2/3/4 door rental is an exponential increase in our cash flow, compared to the single family home we are planning to buy first). 

This is such a personal question no one can really answer it for you, call around to your local CPA's and compare.

Quote from @JD Martin: Quote from @Jay Hinrichs: Quote from @Matthew Drouin: Small wine town is all I needed to hear.Seasonal tourism is usually not a great industry in which to build a sustainable business.There are probably higher and better uses of your capital near high velocity metro areas.We have small wine towns near our city in the finger lakes region of western NY.  

Talk to both and compare.  

It’s free and that is one way to get free listings.judical states also have to file a lawsuit and you can search civil suits or contact sheriffs offices to get the calendar and listing for foreclosurespaying for a site is all in one and maybe worth it compared to how much time you are spending searchjngif you stay in one area then I recommend what I mentioned