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I have comparable experience in Italy in terms of setting up a business and I spent some years in Portugal - by the way a great country, I would have stayed forever too had I met the right woman, but that's another story.
The biggest and most difficult difference you will perceive compared to the US is bureaucracy and taxation.
Hopefully you have a substantial sum already saved that generates supplemental income, and kept away from the euro taxocrats, so that your after tax income generated in Portugal will enable you to attain your desired level, or the business is so successful that you can actually afford to pay taxes without excessive burden.
That's it in a nutshell.
Don't know what part of Portugal you and your folks are going to, but a fantasy of mine is to retire on a small/medium-sized finca in eastern Algarve.
Anyway, all the best!
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