My "scam" degrees earned me a wonderful living and more importantly they provided me with life skills I can use in any situation.  

We already like the area that we live and are familiar with what the house needs having lived here for awhile.I am feeling that we could be in a good "house hack" situation, but I have a few concerns: First, I have to convince my wife that this might be a good house to buy.

I need guidance regarding my situation according to the laws in CT.  

And another one in the same situation that someone wants to sell to you for $95k less than what it's worth today?

Don’t get me wrong, it is my property and I inspect them, I am careful with my word choice to reflect the situation.

It depends on a ton more details about your personal situation.  

It's a unique situation that definitely has some upside.

If you can find the right person in the right situation you can get a deal...But, always a but, you need to understand the value of these properties as well as the solutions you provide.

What exactly is happening in these situations? 

You might even be able to attack the expenses by doing things like metering the utilities, such as water.I believe the key to your situation may lie in knowing the rents/amenities in the immediate area (6 block radius for example) and work to position yourself well in that market.Any chance this is the 8-plex on Gumwood?