Mine died suddenly in a car wreck when I was 16 years old (42 now). 

Okay, let's play this out: Would you not sue a car wash that has wrecked your car just because it's an LLC?

MBR Wrecking, based in Skokie/Lincolnwood.

Contemplating switching CPA's.September- After saving for 2 years and losing it multiple times above buy a new to me car. 30 miles in wreck it.

More often it's just a train-wreck waiting to happen.The biggest hurdle (other than the potential liability, including defense costs when things go south, regardless of what the seller would sign off on prior to or at settlement) is the requirement that HOI (hazard insurance) continues to protect the lender and owner. 

Yes, you can find duplexes at 50k that aren't a total wreck in green areas--there are a few pockets of Milwaukee neighborhoods that you can accomplish this, Riverwest, as Tyler mentioned, being one of them. 

Last tenants wrecked the place and had to spend a lot to get it back up to level before they rented.

If I could go back in time, I would have: bought a duplex/triplex that needed value-add (a wreck).

I would have been a wreck trying to make sure the work got done in a short six months or even a year. 

Or depending on the home's setup, maybe he rents out the entire place and moves somewhere smaller and more manageable.I know thats not ideal but its a LOT more ideal than losing his home and wrecking his finances.