The last owner did a lot of CHEAP repairs that the inspector didnt catch.

Some times you need to catch up the arears mortgage, make repairs, give the sellers some moving money etc.   

The one that could catch unsuspecting realtors is familial status, as that seems to be in every love letter I've ever seen. 

I've been keeping an eye on the market and I've seen a few multifamlies come up that could offer potential cash flow.

You need to be able to catch peoples eye!

He's communicating with you and being honest about his inability to pay, so that's a good start.He won't be able to catch up and you don't want to deal with a tenant that stops paying but refuses to leave.

A month or so later, I see it scheduled for auction at the county courthouse for $282k, and again I think "Too expensive, but I'll keep an eye on it." 

That's what crushes the deal in my eyes and drives me into negative cash flow. 

@Joseph Cacciapaglia Thanks for clarifying, I am keeping an eye out for 2-4 plex for my next purchase.

Keep an eye on the events tab for the location as it changes from time to time, but the meet up is usually on the second wednesday of each month.