I tend to believe that “emotion” and “risk-assessment” can’t be quantified in a spread sheet, yet they are very much significant factors in every investment decision. 

My background is in construction management so not much will scare me off; as long as I can quantify the risk and make the numbers work.   2.

Finally I get the non-quantifiable ability to have a family member close by to babysit.

A lot of investors overlook the deals/opportunities that are already easily within grasp of their existing portfolio.Your analysis seems apt to me, obviously the 'your time' is hard to quantify - I'm not sure that the jump from 2 to 3 bedroom would enable getting less needy tenants - at least with what we're doing - I think this would actually typically be the reverse if I had to generalize. 

If you are more comfortable with your current market or other markets you know well that is not really quantifiable and is more a gut feeling than anything else. 

IMO, there are two distinct advantages to REI: 1) it's a local market, meaning situations vary from town to town depending on many variables that are not simple to quantify using 'national averages'; and 2) it's an inefficient market, unlike, say, the stock market.The economics of the pond I swim in are driven by a growing university system and a growing regional medical center.

If that deal holds, said Von Ancken, it will be the highest price ever paid for air rights in the city.Von Ancken told the luncheon that, while air rights were definitive and quantifiable, he wasn't quite as adept at predicting the future of the real estate market in Manhattan, commenting, "The future is amorphous and is dependent on many variables."

Could you ask Bluehost to quantify what they mean by 'a lot of server resources'?

Of course that is VERY subjective and hard to quantify.

Possibly, they could sue you for specific performance and force you to sell, or somehow quantify the loss they sustained when you did not deliver (hotel expenses b/c of no home to move into, etc.) and (also) sue you for those damages.