In Texas, like @Steve K. said, you are a customer without an agreement and you are a client with an agreement, meaning with an agreement they have "fiduciary" duties to you and you will be properly represented.  

One thing that has held me back is my fear of handing the financials properly. 

So make sure you balance that scale out properly. 

Which means upon default of the sale you do not have to foreclosure, may may take non-judicial repossession.Can anyone confirm if this means you could sell on owner financing and evict upon default with a land trust and proper agreement?

@Evan LoaderYou definitely want a more experienced CPA when it comes to K-1's / Passive investments.I have seen issues where new accountant's will not properly carry over passive loss carryforwards.I have also seen issues where accountants will file state returns where not required. 

Good customers breed good customers, if properly "feed" to do so. 

For either city I am open to long term rentals but would prefer if one unit could be used as a short term rental so that during my visits I can used it myself.Neighborhoods to consider for STR in Chicago Proper- Just about anywhere North of 290 except maybe Austin and West Garfield Park; Some good targets south of 290- Lower West Side; Bronzeville/Oakland; Bridgeport; Woodlawn (Near the University); Hyde Park (Needle in a Haystack); Kenwood (Needle in a Haystack); Grand Boulevard 

I think you're best bet is to learn how to properly analyze multi properties, then find one that you can take down with a partner.

I would encourage reaching out to your REA as well for proper due diligence. 

If you want to do this properly I would set up a mtm lease for each of them that way you can record the income for tax purposes.