@Alex Gruenther,You're stuck in a common "beginner's dilemma".

Rather, you assume that they are in good health unless they tell you otherwise. 

The owner occupancy requirements can be waived when things occur that present a hardship to an owner by staying in the property, things happen that are unforeseen such as a divorce, separation, loss of job, job transfer, death of a family member or where an owner may be required to care for family, birth of a child requiring additional room, some previously unknown issue, say radon gas at a low level that causes some health concern, a child you is found to need a dust free environment can cause an owner some health, financial or other hardship, that, if that matter were known prior to borrowing or buying, the owner most likely would not have carried out the purchase.

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If these sellers are not "wealthier" owners, just mom and pop types, they may have issues in their retirement planning, their health concerns and their ability to qualify for health benefits, holding a note can be a blessing or it can cause a chunk to be lost.

...and the Boston dilemma. 

I wrote my wife a "short story" while she slept, detailing our future (kids, real estate business, barbershop/mentoring center , health/fitness) and the impact we'll have on our future children and the community as a whole.  

These properties sell due to partnership splits, estates where heirs want to cash out, divorce, health issues, relocation, retiring landlord, etc.On the commercial side I have also ran into situation where a developer has built a brand new center.

The dilemma is that I may need the profits from the sale for a down-payment.

While I agree tax assessments have little association with the market value of a property, I do find them to be an indicator on the financial appetite and health of the municipality/city in which the property resides.