Would I be better off contacting the real estate agent that has already shown the property or should I attempt to contact the bank itself? 

I called someone to patch it and he was unsuccessfully after several attempts.

I'm in second lien position and property owner was attempting a short sale which was approved by bank but not all of the liens in time.

In these discussions, is it common to be representing yourself and trying to reach out to seller agents to find properties, and attempting to build the relationship with them?  

Exception would be if they're attempting to create a bidding war, but I believe those are rare houses indeed with something unique/special to offer. 

Hi David Sweeney ,I won't attempt to tackle the many questions contained in your post, but one thing to note is that since the subject property has >4 units, it is considered a commercial (not residential) asset.

I do not have much exerience I will attempt to answer your question.  

I am interested in some help analyzing this house.https://www.redfin.com/IL/Lake-Bluff/136-E-Sherida....It is a 2br/1.5ba Finding anything in this part of Lake Bluff, east of Mckinley Rd, for under $500,000.00 is rare...

Also, the renovations I did on the house were so extensive that any attempt to segregate the appreciation and costs, solely related to the underpinning and 8' basement ceiling height, would be speculation.

I attempted to call an "emergency" electrician, but he never called me back.