I'm OK if it is 10-14 c in winter
In Italy I'd advise you to go to Sardinia (west and southwest sardinia if you're looking for wind and waves, north and south if'you're looking for wind only) or to Sicily (south and west).
If you're looking for a place to live 6-8 months a year, Sardinia could be better
If you're looking for a place to live 365 days a year, you might choose Sicily, warmer and more populated in wintertime
Living in places like Siracusa-Ortigia, Noto, Scicli or Modica and kiting in Santa Maria del Focallo or Pozzallo ... that would probably be the best!
Otherwise, in Sardinia, you could live in the area of cities like Sassari, Alghero Oristano or Cagliari, and be few mins from kitespots like La Pelosa or Chia
Other than Italy, I've a real passion for Greek islands, but in wintertime they are really few crowded, may be too much in my opinion. In this case I'd choose to live near Athens, from what I remember in the coast between Rafina and Cape Sounion there should be some kitespots