Perhaps check on how that works for condos dev down the road as that one could be a lottery winnings like future. 

My career, at least, has a very nice side to it that I would not give up even as a hundred million dollar lottery winner.

Unless you hit the lottery, it's just not going to happen that fast.What you are looking at doing here is making a career change, you're not looking to achieve financial independence.I think it's important to make that distinction so you don't set yourself up for disappointment.

But that is very misleading.It is "possible" in the same way that it is "possible" you are going to win the PowerBall Lottery.

Go buy a lottery ticket .

You're so right about the city's laws and systems, condo lottery, rent control, ellis act, etc etc create a crazy world, and potential windows of opportunity for value creation.. if you get the golden ticket!!

You need to live within 50 miles of a unoccupied STR, you need to be living there, lottery system for new permits and you don't get one, STRs are banned overall in certain zones, HOA votes to disallow STRs.

Hey Jose,I think the visa you are looking at is EB5 ( 500k investment + 10 jobs created for 2 years) , not EB2 (masters or Phd degree with 100k salary , winning the H1b lottery and working under it for 2 years etc) Keep in mind that if you invest 50k, that's 50k less from the 500k .

You're running a business - not a lottery. 

It's better odds than buying a lottery ticket.....