So we shopped it out to our consistent buyers but at a strong price of $75k.

You can compare both options and see which makes more sense with the rate you'd qualify for.

In the case of a successful tort against you, you might regret commingling funds in a single bank account, but I can't see how keeping them consistently separated would ever burn you, even if it is a bit less convenient.  

Hard work and consistent action pay off.

Biggest thing IMO is getting close to the train station and have a high quality units that may not look attractive on paper the first few years but will have the ability to raise rents consistently long term. 

The other qualities of being successful is just consistency, do it daily.  **** is hard, but that's the reason not everyone is successful. 

Can you make good money doing this if you consistently lend compared to owning a buy and hold prop?

It's important not to get too caught up in the details; use the analyzer to compare one property to another.

Additionally the suburbs have higher taxes compared to Chicago proper.  

Half of sponsors are now getting crushed when the going is getting tough, and those previous track records don't really mean much, compared to the things I list above.