At the end of it all, I could be wasting 5, 6, 10 years.I do not have systems in place for short term so that seems to be the longest shot considering the lack of upside.I am not liable for capital gains on this property so that’s the biggest draw as well as freeing up the capital.

(I assume you're talking about her capital gains exclusion, yes?) 

I would love to gain as much hands on knowledge as possible but it doesn't seem like there are many opportunities available near me (North Jersey/NYC area). 

Cashing out to invest in other ways may result in a huge capital gains tax hit plus risk of losing it due to inexperience.

Maybe more.Where you can gain some money in this analysis is in the garbage and water / sewer expenses.

You would want to make sure that their rent payments actually gain you a profit and that there isn't any penalty for selling in a few years.

@Ashish Acharya I want to say it was capital gains tax if you dont keep it for a year or so.

$100k gain is my minimum to bother with an exchange. 

The 3 year mark from the day you move out is important since it will be the deadline you have to decide whether you want to sell or keep this property without having to pay capital gains taxes. - Please notice that you won’t cash flow the $30k (minus repairs, vacancy, taxes, etc.) that you calculated, since you will have to pay interests for the HELOC

The incentive for investors is the deferral of capital gains taxes in stages over a period of years.