There are other riskier assets that I think should go up but they are far more of a gamble so I am using our retirement money for those.

You are gambling.

That’s the gamble...

I guess it’s all a gamble really.

As others have mentioned, I would get into a skilled trade that requires a license that cannot be offshored or done by a machine (plumber, electrician etc).This would set you up for good W2 income, you won’t go into debt, it will expose you to renovations, and you can house hack while you’re young and single.

Part of the motivation is to secure residency in multiple countries, have my investments in multiple currencies, and to set up an offshore structure for my company in one of these locations. 

The investor seller (usually US or Canadian) usually moves out in the middle of the night after he has carefully wires all investment capital to a different offshore bank account... and leaving the investor buyers high and dry.Not much you can do legally when you have been taken advantage of in a foreign country. 

There a few options of what kind of a company you can choose, it can be either a local software dev company, in-house development team or an offshore software development company.

The only way I would consider what you are proposing is if the equity from your coop is enough to place enough of  downpayment (think 50% of purchase price) on a small multifamily (think 3-4 family) so that the income from the new property is enough to cover all expenses of the new property as well as the loan (or a significant percentage thereof) on your personal residence.It's a gamble that can break you or be the beginnings of your real estate portfolio.

Running a successful STR comes down to 3 Ps: pics, people & pricing.1) Decorate your house nicely & pay a professional photographer to take some amazing pics2) Hire amazing people - cleaners, handyman, recruit some neighbors to help fill in the gaps, & self-manage or hire an offshore VA to manage the property if you'd rather make yourself rich instead of making a local property manager rich (more on that here: https://www.biggerpockets.com/... )3) Price fiercely to maximize profits not occupancy (they're not the same thing).