My best friend has lived in the South of Portugal with her husband for over 20 years and had time shares for a few years before that. I have visited them quite a few times and it doesn't impress me. I have felt bored at times even in a short visit. If you play golf and bridge you can fill your time.
My friends now have considerable severe medical conditions and receive excellent medical treatment, but this has to be paid for by expensive medical insurance. They are well off so money is not a problem.
The language is difficult. My friend is bilangual in French and we both did Latin at school so the romantic languages do not pose too much of a problem. She is still having lessons on Portuguese and finds it not easy. I speak French and Italian, I could probably manage a bit of Spanish but Portuguese totally defeats me!
My friends husband is now in a care home due to dementia. The care is good but the carers don't speak English. It's clean, but not full of home comforts as you would expect in a pricey home in England. And it's expensive.
My friend has made the best of what she has been delivered and has an OK life given her severe mobility and other problems. She can afford a lot of care. However she would move back to England to be near her daughter and family, but would have to wait for husband and dog to pop their clogs. She is very brave and I constantly worry about her.I
The climate is changing. She used to tell me how desperate they were for rain. It used to be dry for about 9 months a year. Now she is constantly having rain, and last week she had heating on. When I visited in October it rained every day and wasn't particularly warm. I wasn't tempted to go in the pool.
Compared to my life in France profonde, well, it doesn't compare!!!
I hope this has been helpful OP. Personally I wouldn't consider a move there and only go for my friend. Keep us all posted on how you fare. Good luck.