I understand and appreciate the S&P tracker strategy but end of the day / career means big tax penalties.HSA is a priority for us this year and we modestly contribute to 401ks, employer ESPP. 

Let's just say compliance officers have a hard enough time educating their employers about compliance, so educating investors who don't already know about it, nearly impossible.  

Use umbrella insurance as an additional safeguard, especially if you opt not to form an LLC.Avoid S-Corp taxation for rentals, as rental income is passive and not subject to self-employment tax.

As our team has grown, it's become easier to cover responsibilities if someone quits, goes on vacation, or if we terminate employment, compared to when we had one or two homes. 

There they are seeing both a great job market, a number of large employers moving in, and are still in the top ten of population growth nationwide. 

@Benjamin Ying The only way to cash flow in the current market is to employ a higher effort strategy like STR, MTR, rent by the room, etc.The "cash flow on paper" properties in stagnant markets or C-D class neighborhoods are probably not the type of places that you want to own long term.

Employment Rate: Italy has historically had one of the lowest employment rates in Europe.

Does anyone have experience employing out of town people with 20 plus years experience ? 

I am no longer employed with the Company. 

For all methods you would want to find a market that has strong employment rates, strong income rates for the market, and is a growing or an established market.