I can't say much about flying around Portugal since I'm only into aviation for one year. But from what I know, here in Madeira there are about 50 pilots, about 15 CPL's and the rest PPL. Flying here is challenging, usually, in LPMA windshear is frequent, gusts of 25/30kt. I don't know if you knew this but LPMA is the only airport where it's given you 3 winds. Two from the runways and the other from Rosario.
Another thing that many people from the mainland Portugal are kinda afraid of is flowing over water for miles, but i haven't got any problem with it (so far:wink:) we just follow normal procedure and have a raft on board and wear lifejackets.
In the summer (August) I'll be doing my cross-country flight in mainland Portugal, and at that time, I think, I will have a big picture of what's flying around Portugal. Regarding ATC, Legislation it's pretty much like UK. After all it's a JAA PPL.
If you want to ask something feel free.
Cheers