I would also not attempt to do it out of state, unless you have a very trusted partner in the area.Second, there is the value of your time.

This is my first attempt at a house hack, so advice is much appreciated!

I attempted to double the size of an existing project and my project ultimately went belly up due to my contractor knocking down the existing home.

I assume that the bank will repossess the house and sell it for a loss after an attempt to short sale it?

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.