We will need to mortgage the condo or sell it in order to outfit our home (and my brother-in-laws home) for my in-laws to live privately and comfortably.

Spoken from a wife who's had to learn the long, frustrating uphill, hard way and still learning how -- to step back outta the way, relax, focus on being his wife & just let him lead me .... 

Outside capital has come in and shored up pricing from the bottom up, driving up the lowest end of the pricing spectrum (or as low as investors were comfortable going).

Consider factors like flight convenience, property management options, and your comfort level with the local market conditions.

We also wouldn't have been able to relax early if we were in the hospitality business bnb-ing or midterm renting it out.

I would feel comfortable, as long as owners allow, letting anyone reach out to them or any of my tenants for a reference. 

Now, I think each person has to evaluate their level of risk comfort because being highly leveraged can also create problems if there are significant market shifts.

Is any of that dictated by my state/county, or is it whatever I'm comfortable with? 

I'm beginning to feel more comfortable after the first couple calls, which was great.

Following cashflow trends in emerging markets can allow you to meet your goals much quicker, even if that means getting a bit out of your comfort zone.