I personally own in Racine, and I am expanding my portfolio into Milwaukee. 

The drawback is you need to build trust and relationships upfront.Both have their place, but private money tends to offer more flexibility, while hard money is more structured and accessible if you lack personal connections.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.

I purchase my personal investments to maximize their equity and hold long term.

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Yes I have known it to work because the owner is not a push over, enforces policy and can make it run good......however, do you have the right personality to do this, AND if you move out can you continue to have the house run smoothly with no one in charge.  

I personally started in my local real estate market in Columbus Ohio.

Account holders can't take any write-offs personally for investments made in the 401k.

I've done enough personal home projects to know, if I find a deck company it'll be 2k, but a GC will charge me 2.5k to over see it...

You'll want to put together a personal financial statement (basically lists of all your assets and liabilities) and have your tax returns ready.