Hi Steven,It sounds like you and your wife, Renee, have a wealth of experience in the real estate and construction fields, which is a great foundation for starting your real estate investing business.Given your background in residential remodeling and home inspections, and Renee's experience as a real estate agent, you're off to a strong start.

Any insights or experiences would be greatly appreciated!

Some questions for the people with experience: What are some basic landlord problems I will most likely run into?

Definitely ask if they have experience with this. 

Keep sharing your experience :D

Confirm that the provider has experience with the particular investments in which you intend to invest your retirement funds as you very likely will have questions in terms of the mechanics (e.g. how do you invest in real estate, etc.).4.

(been working and succeeding since 2008 or before, someone you have experience with, good returns, close to 5yr investment?)

Use your superior knowledge, experience and analytical ability to spot something in a property being offered for sale that everyone else has missed.  

It’s definitely exciting to see suburban Chicago getting recognition as a hot rental market—it’s something I’ve noticed in my own experience as well.

This conversion will begin at the end of the month.I am just sharing the above to give context to my level of experience with this type of investment.I look forward to hearing from you all.