@Ben Healy I would be concerned about a Heloc to buy a hold because of the nature of Helocs. 

It seems like many smart locks have too many bells and whistles for this application.Because the basement currently can be accessed by anyone -- I don't want to make any assumptions about who has left things hidden in my basement ceiling or who may or may not be trying to smoke in a basement with natural gas heating fixtures.

Alternatively, would you choose to keep these expenses since an HOC could in theory require a 1x fee if they are short on funds and need to do a major project like replace the windows, pave the parking lots, etc?

Obviously the lower starting prices in the latter areas potentially give it a natural edge, but not sure if the PLG/Prospect Park South neighborhoods are still a whiles away from meaningful price growth.

I bought some property with 2 houses and an apartment. At the time one house added 0 value to the mortgage, I went to refinance the property and I was told I could not refinance due to the second home having 0 value. ...

Many of our clients invest into alternative assets both inside and outside of their retirement accounts.

Separating electrical will be a different process and cost than separating heating where you might need to run separate natural gas lines and purchase individual furnaces.

Open to other alternatives as well! 

✓Second Home Requirements must be occupied by the borrower for some portion of the year is restricted to one-unit dwellings must be suitable for year-round occupancy the borrower must have exclusive control over the property must not be rental property or a timeshare arrangement1 cannot be subject to any agreements that give a management firm control over the occupancy of the property must be underwritten in DU and receive an Approve/Eligible recommendation, with the exception of high LTV refinance loans required to be underwritten in accordance with the Alternative Qualification Path (see B5-7-03, High LTV Refinance Alternative Qualification Path).

I've been debating to turning it into condos, but don't have much insight into establishing an HOA or anything of that nature