Additionally, I appreciate the note on Madison's strict short-term rental regulations for non-owner-occupied properties.

Sorry the copy and paste is horrible and I don't know how else to fix without having to just type it out :(.ABANDONMENT:Tenant covenant to occupy the Premises and shall be in default if Tenant does not occupy the Premises on a regular,continuing, and consistent basis unless otherwise agreed to by Agent in writing.

I am looking at structuring a deal and I'm worried the DSCR will be too low and the deal may benefit from restructuring by purchasing the 2 vacant out of the 12 otherwise occupied units with hard money as opposed to trying to purchase all 12 with a institutional loan just because I'm worried the 2 vacancies will drag down the DSCR for the new purchase.    

Those loans are meant for owner occupied primary residences. 

Owner occupied only.

I'm financing it as a second home (since I'll occupy some of the time and rent out when I'm not there), through a conventional mortgage.

As an owner occupied home, you can sell and take the profit tax free. 

My family is in the initial stages of a move to Japan and  applying for a business manager visa.

It currently has 14 out of 17 units occupied, generating a monthly income of $6,300.

The longer you drag this out to save a few more bucks the longer it will be before you can have this occupied and earning you money