Not the exact answer your looking for, but if you can answer those questions, you should be able to pick the towns that best fit your tolerance level/skill set.

Assisted living doesn't seem like the best route for a house, as it requires medical considerations, and staffing.

i heard somewhere where 75% of American live paycheck-to-paycheck. i even heard a stock broker say a lot of his clients live the same - we're talking HUGE salaries too.we don't know this guy's situation. maybe he has medical bills, child support, yada yada. it's not always people spending beyond their means - though that does happen a lot too.

She is unemployed and will stay that way for at least 12 months due to a medical issue. 

You are going to hone your skills of recognizing what a DEAL really is.

Someone else frequently has contacts or opportunities or knowledge or skills we lack.

TLDR: To hedge against downturn, buy right and learn skills.

In Baltimore you can buy a house for under $10,000 and rent for $300-700, that's good cash flow, you may not want to invest in that area.Cash flow in my opinion is a function or your negotiating skills, your ability to use power prospecting methods and to create leads that make sense.

With the knowledge you have it does sound like you just need to jump, or perhaps even work with someone with complimentary skills. 

It turned out to be a turnkey property that the owner needed to sell fast to pay for medical expenses.