I am literally open to any good opportunity to house hack (or at least live for cheap while renting), anywhere in the Greater Boston Area (although I would prefer the North Shore, and not TOO far north. 

There is often not a direct correlation between some of these systems because investors think that conditions are only temporary and thus they factor that temporary status into account when determining what is a 'fair' price. 

Oh well, people will treat your property as a temporary storage and crashing place, cant do anything about it.

While we have visited and may have to move at some point, we decided to shore up our assets while we still have steady employment income.

Both of these could be temporary issues but there is no guarantee of the outcome.Overall housing prices are up pretty dramatically from the bottom.  

Clair Shores near 11 mile and Jefferson!

ALE offered $350/mo over my normal rent to place a temporary tenant in the property, along with my normal Security Deposit. 

Currently, I'm looking for a 4-5plex in Montréal, or on the North shore.

Clair Shores.

All I can say is there are more than 1 way to value a property, IE. by its gross income, location, comp. sales, Etc....What you are describing has happened as a result of multiple short sales taking place in a concentrated area and I feel has definitely caused somewhat of a bottleneck for prices to run up but should only be temporary....would like to hear others weigh in on this...best regards,Chris