It is within driving distance for you, which can be very helpful if you want to check on the property, if you have an emergency or if you are planning on using the property occasionally yourself (which most people do, it's a great perk of owning a home on the beach).

It would also have to be mowed occasionally to keep the weeds down.I have a tractor and all the equipment to maintain/fence/etc. for cattle but it appears that wouldn't be arm's length even if I did the labor for free. 

Broken handle on the washer/dryerLight flickering and occasionally not working in the kitchenBlinds that have some missing pieces/cracked elementsBurner on stove not workingThese all seem like items I should pay except for maybe the first and third ones.Really appreciate getting the opinion of others here as I figure out how all of this works!

I need someone to come out twice a month and do a basic cleaning/sweeping, occasionally cut the grass, etc.Any referrals would be appreciated.thanks, lenny

Yes, there may be the occasional idiot that is a millionaire in Wisconsin, but that's generally someone who won the lotto or inherited their wealth and they are the exception and not the rule.

I would like to pick up rentals as well as the occasional flip.

The terms we have agreed to are thisPrivate Money Partner bring the 20-25% down payment, does NO active management other than voting to approve the purchase, and occasionally voting on major items such as time to make large cap-ex purchases, time to sell etc....We do ALL of the work of finding, funding, rehabbing if needed, placing tenants, all ongoing PM and business management. 

@David OlsonI am in no way an expert at this but I believe when you are making a cash purchase the main team players are:Attorneys, Title Company, Inspector and Appraiser (occasionally)Attorneys: Using legalese to get the purchase contract in writing Title Company: Perform due diligence to make sure there are no liens against the propertyInspector: You already covered thatAppraiser: To determine the price of the property at its current state and after repair value.

Everyone needs to vent occasionally though I guess ;)

It is worth considering areas like McKinley Park (right next to Bridgeport and also becoming a Western extension of Chinatown), West Pilsen (still seedy enough to yield an occasional good deal), or Bronzeville (again, pockets of dereliction open up the opportunity to help clean up your own little corner of the neighborhood).