In the absence of some good advice from your agent your "gut feeling" to pull out on this one might have been the right decision.   

If you are having problems getting it rented or your gut is telling you he is legit or you really want to rent to them for some other reason just get a big extra deposit.

The house is in very bad shape and would be a complete gut but in a decent nerighborhood.

You need to know your numbers and you then will know what you consider a good deal.And no, 250k for 3 or 4 housing units in a good neighborhood of Chicago is not possible unless it's a gut rehab. 250k is the price for a basic 2 bedroom condo in a decent neighborhood.

For some reason, my landlord instinct kicked in and i started thinking "thank God he didn't die in your unit". 

But I also feel like someone here may be able to explain why my gut is telling me that’s a rookie mistake.

Put ~100k into it, it was a foreclosure and needed practically a full gut renovation.

They were there for six years before I took over management so the damage was done and we kept them as long as possible, knowing we would have to gut the place when they left. 

We have multiple projects that we are working on, ranging from full gut reno's, to smaller fix-and-flips, that we could use additional contractors to expedite and grow our company.

Someone who has great investing instincts but who will also not be on the hunt for the same good deals?