You reference future events that have already occurred.

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

If you want to look at total expenses over the years, you need to look at total income received as well with your potential sale price. 

At that time we could renovate the ground floor apartment and potentially turn it into (2) apartments for a total of (5).My questions come down to how do we deal with the existing 40k mortgage, whether we can make it work so her parents aren't paying much in rent, if anything at all, and whether or not we set up any legal entity, like a trust to help the legal situation of paying off her sister down the road. 

Hi @Derek Dickinson with your skills New Jersey has huge potential. 

@Chris RossMemphis is a solid market with great investment potential.

Your goal is to reach as many potential buyers as possible, and right off the bat you're limiting your pool of buyers.

Additionally, timing the sale in a lower-income year or exploring potential deductions could further reduce your tax liability.

All you can do is work with what you know now and what is a reasonable expectation for the future.

Would love to connect in the near future and hear how your first flip went!