So make sure you balance that scale out properly. 

My desired criteria are as follows:-At a minimum breaks even as a house hack-4+ Br single family OR small multifamily-Safe area (I don't have to worry about going for a walk at night)-Within 30 minutes of Columbia (maybe 40 minutes if it is towards DC)

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. 

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 joined a few FB group pages last night and will begin to enter more. 

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

It long term rents around $2,100/mo, and they believe it will rent for $200/night, and generate $3k-$4k gross per month (we know we'll hit at least $3k and that's conservative).

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.