@Cole Starin sometimes it makes sense to sell the WORST property in your portfolio.Another option is why do a LOC on the duplex, when you could just do a $100k cashout refi to pay off all your debt AND keep the property?

Who is picking up the croissants and dropping them off at your place?  

I heard lots of scammers also trying to go off the app and then they say now need to evict me which takes 6-8 months in Chicago. 

There are smaller one-off groups as well. 

There are good relations with the neighbor so this likely wouldn't be terribly difficult to pull off, but I haven't ever developed a property from scratch so I would definitely like the opportunity to partner with someone on this to help ensure the success but first I want to finish the smaller property to have sufficient funding available if it is needed.

It's paid off, and is currently held by the trust she and my grandfather set up.

You're better off self managing or going with a local company with boots on the ground.

First off congrats for looking into this realy estate stuff at such an early age! 

Off-market, agent-listed, or are you networking with other investors who have deals lined up?

I have been paid off by Cogo loans so I know it happens.