Additionally, for each existing and future Illinois investment property, I intend to:- Deed each property into separate Land Trusts.- Establish an Illinois LLC that will be taxed and will own the interests in the Land Trusts for my Illinois properties.- Set up a new management entity taxed as a C corporation, which can be fully owned by my revocable living trust.

There is a lot of really old housing stock in our area, but I really thought this would stand out.

This also allows you to be involved and gain experience for the future. 

Going forward, what is the best way to structure the partnership so we can 1031 exchange in the future?

Oakland scares me, considering renting out my home if I decide to leave the USA for a lower cost of living country in the future, although I know a few people who bought in 2008 renting their homes out in Oakland and doing well. 

We're short now, and very short in the future. 

My current plan is to take my time in finding a deal that either offers great concessions  or that can be negotiated down in order to make up for a possible price drop in the future.

Hello, I have 5 mortgages on 8 investment properties, but I'm no longer working a high income job and so I need to pay more attention to DTI for future loans. 

I would cut my loses (and potential future loses) and sell.

@Kamryn DeVaultTo invest in a duplex, consider factors like neighborhood quality, economic stability, safety, property condition, cash flow potential, financing options, tenant screening, lease agreements, future potential, legal and zoning considerations, maintenance and management, networking, and starting small and scaling.