I'm working on increasing my income to hopefully invest in future properties, and trying to help my friends and coworkers on the path to home ownership since many of them are renters in their 20s and don't know the options that are really out there.Here is where I'm stuck: someone I know is currently renting.

In about four months I should be in the Jacksonville NC area, so I have become increasingly interested in that market.

I should have bought more and more aggressively when I started out 5 years ago (again due to view point as a hobby) and not because of price increases over that time, because thats 5 years of semi-passive income and appreciation.

I read early on that doing this increases on-time rent collection by 30%. 

Liabilities increase the basis in the partnership.The allocation of the loan might increases your basis in the partnership but not your partner. 

This price increase kicked me in the butt and made me do it.

Today, those Studios rent for $1,900 each.So each apts moved from $500 to $1,900 in 17 years for a increase in rent of $1,400.If you bought a cash flow property outside NYC that was cash flowing $500 per month, but only doubled in the 17 years to $1k per month, you would still be short $400 per month because your rent increased $1,400 versus your outside cash flow property which only increased $1k.I can't emphasize that if you instead bought our place to live here rather than rent, you should think of it as hey, I'm actually doing better than the above scenario of buying outside cash flowing properties!

If you have the ability to make any changes to your current property that will increase the value, you may want to consider those as well. 

I am trying to figure out how to exit this investment with limited tax liabilities, each property has increased in value by 500% since I purchased them. 

Your way around it if it is fix and flip is to just do work that will increase the appraisal: improve curb appeal, enhance the kitchen or bath, or turn it into an open concept.