So I understand your point of not getting hung up on the numbers but isn’t conducting a proper calculation a heavy decision maker when analyzing and seriously considering a property?

If you have roommates get a proper lease to deal with what happens if one leaves or one doesn't pay rent.

Even as I was working out the deal I wasn’t sure I was working it properly; now I know it’s one of many creative methods of acquiring properties.

If your lender has ANY hesitation on how to structure this properly...then find another lender.

If there were multiple offers on this house, you should be glad nothing major was found and move on.However, just an FYI - if there was not multiple offers on this property (minimum of 5) for a house in Madison proper with a price of $170k, that is a major red flag these days. 

The fact they are complaining online might be an indication the property manager dealt with them properly so be sure to ask the manager for their side of the story.7.

If you can get away without earnest money bumps that's better too, but if the seller is advised properly they're likely to want to add increases in earnest money over time as you get in to your feasibility and have risked some of your pursuit costs.  

When selecting the proper deed from always use a Grant, Warranty, etc. but not a Quit Claim. 

He didn't have the proper car insurance and the homeowner insurance wouldn't cover it.

Your home inspector will be able to determine if the gas burning appliances are vented properly.