The only concern with that is I wanted to have some higher end finishes in the upper level (mainly appliances and glass enclosures on stairs) that would be subject to a higher degree of wear and tear with a tenant. 

In the situation again the whole sale would be subject to long term capital gains. 

Cash Out RefinancePros: Extra 5% mentioned above, somewhat more liquid, its 'mine' if the housing market does crash, keeping slight bit more leverage                    Cons: current inflation, 'higher' mortgage payment, closing costs each time cashing out. Line

I just started a separate thread on this subject.

The subject property is 4 standalone buildings spread across 6 different parcels of land (3 parcels contain the 4 buildings, and the other 3 parcels contain surrounding land).

These are properties that have sold near the subject property with a similar: build/construction type, lot size, building size, interior condition, property type, year built.

Yes, there are adjustments for the differences between the comparable sales and the subject property (your property), but they are relatively subtle adjustments because they are using "comparable sales".

Also, if you search the forums for mentors there has been many posts and comments on the subject in case you want to explore others comments.

@Adam Diaz, Estate sales are often subject to total unanimous agreement from those who have inherited the property.

The subject property is the only eyesore on the street, it appears to need mostly just cosmetic interior/exterior upgrades, and it basically pencils out at 7 units-- with an 8-unit conversion it will allow a refinance of most or all of invested cash within 2 years.