First, no apologies needed! Please ask questions, we LOVE to talk orchids!
Most Cymbidiums are fine with cold - even down to near zero if acclimated. I think you can just grow those outside all year around. If you went to see just how tough those are, check out this website, from a southern California grower:
Ice
Laelia anceps will also tolerate near-frost. Where I live, winter temperatures are just a little bit more temperate than yours (but each winter there are a few nights that go below 4 deg C) Days do get warmer (18-20) but that's not exactly tropical... My website (link in my signature) shows what I grow, and the Index of Plants indicates what grows outside for me, in a climate I think is quite similar to yours. (Another Mediterranean climate area!)
The ones growing outside live there all the time, so as the days and nights cool off in the fall, they adjust gradually. That is very important - they can tolerate a lot if change is not sudden.
Brassia rex grows for me but doesn't bloom. However, Brassia verrucosa (one of its parents) grows and blooms very well for me. Also some of the related South American species in the genus Ada (which are now also Brassia) do quite well. So there are many to choose from.
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