Right now you wouldn't have any problems at all to access betting or poker sites, but read about a new legislation that was about to be passed for online poker (which, if I remember correctly, was a first step to a segregated player pool like in Spain). Besides that there will always be ways around it, especially once you have an active/verified account set up.
Portugal def. is worth a look, it's not that cheap like some websites make you believe, but it's def. cheaper than other Western European countries and if you take the infrastructure, security, food, nature/beaches & climate into account, plus like you already stated easy accessibility to lots of other great places within a 2-3hr flight, it's a great place to live at.
Even though, personally, I'm not sure if I would choose the Algarve or opt to live in Lisbon.