I guess what iam asking is.. do you look for massive headaches like this pig in your market?

If you have it under contract for $120,000 and it only needs $10,000 in work to be worth $250,000 why wouldn't you fix and sell it for a massive profit verse wholesaling it for much smaller profit?

Living in Pai for 3-6 months of the year without needing to pay rent is a massive thumbs up (especially when I'm not earning an income right now) Currently Pai tourists are catered for by either cheap hostels or high end hotels.

The tuck pointing work that needs to be done is massive (basically taking apart exterior walls brick by brick and then putting them back).

It would at least require full permits and possibly a zoning variance or change since many small multiunits in Chicago are massively underzoned and only exist because they are grandfathered in.

I don’t see a lot of downside for you unless you massively overpay!

I remember the days when massive apt communities were giving away free tv's AND a free month's rent to fill a vacancy while houses or my smaller townhouse communities were filling quickly for top dollar with recently foreclosed on homeowners.  

Maybe a syndication would be passive or Reit compared to regular landlording rentals.However since you live in a massive market ( 20 million) there would be many other business options available to make 7k a month that might be passive ish and could be done with just 50k alone. 

That said, I’ve completed three npn deals successfully with embarrassingly good returns.Scott gives massive value, much of it for free.  

You have to take massive action.