Have not "shopped" for insurance. 

According to what I read online, Keen State in NH has declining admissions, Plymouth has been stable, and UNH has actually increased.

Taxes, insurance and mortgage. 

Specifically, can I attract a certain type of tenant - long term, stable, good income, low wear and tear, etc.  

If you want to sell the property, you'd have to release your own mortgage from your NPN to convey clear title.In my experience, it's difficult to find title companies that will insure title on HOA lien foreclosures.

Didn't he have title search and title insurance? 

Buying as a primary residence gives you a lower interest rate, lower insurance and starts building up credit and home equity that you can borrow on later. 

Between having minimal liability risk in my own personal activities, renting to only the very best tenants, having excellent independent tenant screening, long time property management relationships, adequate per property insurance coverage and tack on umbrella coverage as/if necessary, I am more than adequately covered.

Old age is expensive and you need to insure your investments are more than sufficient to take you to the end.

And a lot of the little guys don't have insurance to build more than a duplex.