Your last sentence, "It is much better to lose the property to a competitive bid than to lose it to the bank later" is an important one to be reminded of frequently as an excited newbie to investing. 

My concern with these unit was the life of the units and how hands on the maintenance need to be and how frequent. 

This occurs frequently though & I’d like to capitalize if I can.

Frequently fall asleep with one airpod in my ear streaming BP podcast and my phone in one hand with a not-so-random zillow listing open. 

Deal breakers would be things like they dont specialize in the type of deals you will be working with, the structures they have used have been challened frequently and not held up (i.e. their track history is mixed), or they arent properly licensed.

This question is asked multiple times every week and is getting more frequent. 

I would encourage you and your client to keep moving forward in difficult transactions as that will happen frequently with good deals, especially for flips.

Next time you are down in Chicago let's meet up or vice versa (2nd half falls on me Im back in Elgin frequently).

We used to frequent the beach/ boardwalk which is about 20 miles away, now we're hanging out by home and almost never drive that far unless we have to.

It depends on whether it was technically a lien auction under the new rules, or a tax certificate under the old rules, but people frequently call them tax liens.