REI Newbie from Chicago area - Hello and input.

[Robert Posta]

Hello BiggerPockets members. I am sure you all are very busy and I appreciate anyone that takes time to read and/or respond. I am literally a newbie to real estate except for the 4-5 home purchases I have done for my own personal property over the years. 

I just started reading "The book on rental property investing"  
2nd up is a book named "Rich Dad Poor Dad" .

I am a proud business owner of a 13 year old logistics company. I have always been interested in REI. I am 47 years old and at this point my goals are passive income at retirement and to get away from this desk at times.

I have some cash and home equity to use if needed to get me started.
Income/Cash flow would be nice but is not a necessity for my case until I retire in say 15 years.
I would like to build equity and shoot for some properties that need some work, fix them up and then rent them out and HOLD them. 

I have been trying to analyze properties right now and read up on REI material. It is hard to do when I have no base knowledge of what repairs/renovations cost. I guess all that comes with constant working at it. I am thinking at first maybe I should look for homes that do not need as much work. Many of these homes are very old ( 100 years old here in Chicago area ) and need a bunch of work. Old pipes, possible lead paint and asbestos issues. Not sure I should be heading down that road quite yet?

My initial thoughts are to try and find some homes that are 50 years old or less that may need updating.
First set of goals are to possibly have two rentals in the next year. Initially my goal is maybe to get 5 properties under my belt and then reassess and make a new goal. I am interested in single family, duplex, three flats. I am also looking into joining some groups and will try to attend some meetups about REI in my area.

Is it best that I stick in my own area at first?  Or should I possibly dabble with out of state properties with due diligence in finding good management / contractors out of state?

Would love to hear your suggestion on what I might tackle based on the above info ?

I am glad to have found BiggerPockets. Thanks to all that contribute. 
I hope to one day help people the same as many members are doing.