Perhaps the landlord was suffering from dementia and the tenant took advantage of this?

I'm a native so the prices are... the prices but I too suffered sticker shock when moving from Millbury, MA (out near Worcester) to Newton, MA back in 2013. 

They use this as a sales tool to show they are a better leasing choice because they offer an additional benefit--renters insurance--at no additional charge to the tenant.For those others reading this post, renters insurance makes sense for the landlord because:It includes liability coverage, which can be something for the landlord to pursue under some circumstances if the tenant causes damage to the premises.A tenant who has renters insurance and suffers a catastrophic loss, such as natural disaster or fire, will collect from its insurance.

Even  if market prices  go down as long as you do not suffer a serious reduction in cash flow you should be OK. 

What happens if someone slips and falls on the property, suffers a horrible injury, sues for $1 million, and wins?

Am I too paranoid and suffering from paralysis of analysis?

I'm still evaluating markets at this time but to be honest I think I may be suffering from paralysis by analysis.

Areas who just leave it to chance, will suffer.

The best part about a month-to-month is that you don't have to suffer 11 months of a bad tenant.

But the more you invest in areas where there is evidence of stable cashflow and demonstrates a resilience to rental losses or reductions over a LONG HISTORY, the more likely you will continue to not suffer rental losses during economic downturns.Same with Expenses.