I currently own a primary home and a secondary that is a combination secondary home and rental in a Florida condotel complex.

I walked the property and noticed that it was creating a swamp, rather than functioning properly, and pulled all septic permits since 1969.

Combining the equity with a loan will maximize your buying power and your ROI.  

@Daniel OKeefe Based on the responses in this discussion, it looks like an appraiser would use a combination of appraisal approaches to determine the value.

Likely a combination of several...  

Will you buy and hold, flip, wholesale, or a combination of all of these.In Maine, you do not need a license to engage in any of these activities.  

I am new so maybe I am being stupid, I don't understand why all these things can not be combined into one nice little package (and if no one is doing that right now I think I see a business opportunity for a few of us) Here is the big picture the way I see it, as long as a goal is reasonable there is no reason why it can not be accomplished by you as long as you do the same  things in the same way other people have done who got what you want before you. 

At the time, it rented for $2300 (both sides combined) on PITI of $1550.

Other than that, nothing functionally wrong.

Even when it's not directly price, it's almost always a form/function problem (which still ultimately means it's not worth what you're asking in it's present floor plan, design, use, etc. so it still ultimately boils down to price).