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

Even if he didn't take depreciation they can still say it was allowable and want it back anyway unless he made a statement that he would not be taking depreciation which is very rare. 

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

In my experience good contractors rarely have to get this creative​ to find​ jobs.

@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.

I would love to have a ton of multi family but they are rare and hard to come by in this market.  

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.  

If you have a high barrier to initial rental, you rarely have to worry about things like that.

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.