I've always been a fan of the working for free method in the beginning to gain experience (i'm a resident physician and have been doing this for years essentially).

Honestly, people want the capital gains.... 

Some of my properties have probably gained market value in the last few years since I bought but I don't want to make that assumption in this analysis until I have a new appraisal.Taxes have NOT been taken into account, but I think you all know that real estate beats the stock market hands down in this category.My biggest takeaway is that you need appreciation to achieve outstanding returns in real estate. 

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). 

@Harry Maxtens - pay very close attention to the markets around you.

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

Perhaps by bringing attention to it at a public meeting the "right" person will hear you/get wind of it and send one of their guys out to spend an hour to "make the problem go away."

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