Red flags for me include people who are overly optimistic without considering risks or those who don’t seem to have a clear plan for their contributions to the partnership.

By tackling them early on, you minimize the risk of missing critical dates.In my experience, closing a deal within a specific timeframe requires meticulous planning.

They are holding the proceeds from my sale and I am planning to buy a couple of DSTs shortly.

If you plan to live there in the winters, you might have a hard time doing long term rental outside of that and finding a new tenant every summer.

Provided I can establish a solid investment plan tailored to their financial needs/comforts such as debt ratios and income, they would be more than happy to offer me some financial control.Additionally, If I wanted to, for the sake of building my own personal wealth, I admittedly have the luxury of taking a loan from my parents.

If you plan to manage remotely, then find a good PM or have a trusted team that can inspect your property regularly - and be ready to pay them.

Expect to remodel kitchen and baths and put new floors down, paint, knock down a wall to open the floor plan. 

My girlfiend and I are looking in La Grange and Brookfield which is not quite as fast west as you, but my aunt lives in Wheaton so I am quite familiar with your area.What's your game plan over the next two years? 

The best advice I can give is this: if you weren’t planning on RE would you go to college?

To simplify the existing lease I thought about asking the tenant if they would be ok modifying the addendums to get rid of the resident benefit package and the building protection plan.