Self employment and cash-based employment (that is not being claimed on tax returns) are exceedingly difficult for lender to lend to in most circumstances due to regulations put in place after the 2007+ Global Financial Crisis.  

Reasonable prices, strong rental market, low property taxes, vibrant downtown.

Have you found life in a mid-sized city palatable after living in a major global city? 

I think you're forgetting that in today's Global Market, everything moves faster...so I believe the next one should come in the year 2075... but my math might be off.

In my case, I really liked my job, the sector and the travel that went with it (IT management for a global investment bank after a career in Silicon Valley).

But ATL is also a totally different beast...much larger metropolitan area, bona fide global city, and it still has a very positive trajectory. 

I also think Sunnyvale downtown is more vibrant than it was 5 or 10 years back.

Consider AI and institutional investors, regulation changes as well, it is possible for strategies used today to be highly illegal in the future.We all have hind sight, students today will be in a purely global economy, what we did in the past is not very "forward thinking".In fact, I'd go further for him to consider Engineering at A&M, Engineering and Law at Purdue!

I'm currently a project manager for a telecommunications company that provides construction, engineering, and professional services for several national and global companies.

Color makes a place memorable, yours are certainly vibrant though.