Run a "worst case" scenario and see if you'd be comfortable for a year or two.

Manly macho men tend to believe comfort shouldn't be a consideration.

When you feel comfortable, and have the time to dive into real estate (college can be busy), I would use the money you saved to start it. 

That should put your sale price at around 100,000 to cash flow comfortably. 

I realize there are risks in real estate but I feel much more comfortable owning cash flowing real estate then the stock market. 

Obviously you’ll have to honor existing leases, but looking towards the future, you need to feel comfortable that 850 or 1000 or whatever is a good rent.

The pros include, my wife's comfort.

But at the same time, if the working from home trend continues, the suburban and rural housing markets may not be able to meet demand as people flee crowded cities to a more comfortable work environment.

I have been passively looking at the small multifamily homes for a house hack, but the biggest hurdle is finding one in an area we both are comfortable to live. 

Depending on your goals, investment strategy, and comfort level with outsourcing, the flyover states can offer great potential to earn a quite attractive return on your money!