I don't care about curb appeal or estimated growth as I don't plan to sell and trying to project 20 yrs out is not realistic.

Heat pump units are more efficient than window or portable air conditioners, more aesthetically pleasing.

The goal would be to maintain the curb appeal / authentic look, but at a much lower replacement cost.Thus, I'm looking to find an insurance agent / receive quotes that understand this dynamic.

The cash-on-cash return is very appealing and the entry cost is obtainable for me at this time - roughly $150k per 4plex. 

Spend a little extra time to increase your curb appeal.3.

A pre-ordinance (built before July 8, 1957) residential building or building of mixed residential occupancy, not complying with the requirements in force and applicable to the building at the time of its conversion, may be altered so as to legalize one dwelling unit, in addition to the number of dwelling units originally authorized, providing that said unit was determined by the office of the zoning administrator or the zoning board of appeals to have existed prior to July 8, 1957, and provided such building complies with the other provisions of this chapter.

Focus on curb appeal, and finishes now.

That would appeal to many people.

Get the Seller under contract (electronic signature since he is in a different state; not the most appealing or best way, but it's something as I can't secure the deal without it (obvs); get them under contract for the remaining balance + an offering I do for my pre-foreclosure homeowners - I give them 10 - 15k.

Was there a specific reason - aesthetics, trying to use up space, (not sure if "the land and asphalt all add up by adding 10 ft" fits here), etc.?