The new reality is that there are fewer people going into the trades and the good old timers are starting to retire.

My employer gave me shares of company stock (company is owned by private equity firm, not publicly traded).

- Is there a way around the 30% withholding - I understand I can elect to pay at US personal income tax level if I can prove my business is "effectively connected with a US trade or business"?

And like everything there are trade-offs and not working with an agent definitely has downsides.

Your tenant request to trade work for rent is a clear indication they will not be able to afford rent and you will definatly need to get rid of them.

These are financial institutions that I like to describe as "E*Trade with different paperwork". 

I would say partner with someone, but it doesn't sound like you're a contractor... maybe look into trade schools and find a side gig? 

You can, after all, spend time researching investments and pushing the buy/sell button on your stock trading IRA, as a comparison.The issue becomes one of scale. 

While my background is in software development, I’ve spent a good amount of my free time trading equities/options, learning finance, and now looking into real estate.

Otherwise,  sell and trade that equity into some cash flowing properties.