Moving to Portugal in 2019

Hi my name is Gail and I am planning a move to Portugal this year. I am looking at either Lisbon or Porto area. I am from Napa Valley California and  experienced in wine and food. I have been reading that Portugal is upping their game in wine and seeking English speaking wine educated personnel.
I have lots of questions on many topics.

Seeking info on how to become temp resident. Is it best to come over on a vacation and stay up to 90 days and seek out my desired area and apply for temp residence there? Requirements for temp resident?

Would love to hear from the expert expats to hopefully make my move easier. I am retired but want to work in the wine industry.

Porto or Lisbon for wine opportunities?
Lots of financial questions? Social Security here in the US, can I transfer?
Housing

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