I think this is a calculation a lot of homeowners are making right now--especially if they have a low interest mortgage, equity, and their house will cashflow as a rental.The choice is a personal one of course, but I think your future self will thank you if you pull out some equity from your existing home with a HELOC for the downpayment on the next house and a cushion renting your current home, use a property manager as you have other things to do, and buy the next house and do the same thing again.

I have a 2-person unit with a glass top dining table and it has worked well.

To get started, continue learning through podcasts like the BiggerPockets Real Estate Podcast and books like "The Book on Rental Property Investing" and "Set for Life."

Personally I would just get the proper licensing and insurance if I wanted to manage properties for others. 

You can probably meet him in person if you attend the next HH.

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

Quote from @Amanda Dobbs: Is there a place to find Private Investors as in one person?

@Ryan Raven most states don't care if you screw up the management of real estate you own personally.The government does have a problem with an unlicensed person/company screwing up the management of properties they do not own.

You can find it through the MNREIA web site or email me if you have any troubles.Type @ and the first few letters of a person's name to link.

I am new in this game and here to learn everything.