Northern Spain is in the lead right now. Both me and my better half had set eyes at Gijon without knowing the other one did the same. Very mild winters, mountains with famous climbs, seems very cheap to rent an apartment. It ticks all the boxes I guess.
It might be raining a bit more than you would like. Compare Gijon to Oviedo. I know there is no ocean in Oviedo but you might like it anyway 
It sounds very interesting. I adore both this countries so I don’t know what recommend to you
Did you watch the Camino in Galicia last week O Gran Camiño opener called off amid heavy snow | Cyclingnews
The South of France although sunnier had a feel like of -9deg C in the race a few days later 
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Hello, I’m from Lisbon, Portugal. Let me try to answer your questions. I believe living expenses in smaller towns are pretty cheap relative to other countries. House renting can be around 500€ monthly for something like a T3. Not sure, but you can check on sites like idealista.pt and cost of shopping stuff you can check continente.pt e.g.
(The weather is usually not too cold and not too hot, but we do get some rain in December mostly and cold starting from December going colder into January but sunny until march. Humidity is high and the cold seems colder than it is. Temps from 3 degrees celcius to 30 something in summer, but most of the time of the year it ranges from 14 to 24)
As for English amongst Portuguese, I’d say its very very good, specially in younger people,but also with older (and I mean above 50). And we are usually very appraised for our hospitality and willingness to help.
Some also do some french… specially some older people and emigrants (when come back for vacations), but yeah… spanish is really not our best… we can understand some of it (some is similar to Portuguese) but a good amount is very different.
Any other questions you might have, please feel free to ask me.
Best of luck,
Miguel
edit: oh and has many races with very beautiful scenery. Climbs in Sintra, Douro, Serra da Estrela and also many flat roads as well. Check out all the granfondos we have and volta a Portugal and volta ao Algarve, etc.
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is that in Portugal? lol… 
Ah yes… I found it. Yes, well that is one of the coldest and farthest from the cities places in Portugal. And we did get a yellow warning of an unusual lower temperatures for this weekend.
really really remote…
Yes Trás os Montes!
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Lol that’s my parents’ (and by extension my) home there. Serra do Larouco summit is only an hour from our house so it can be a cycling paradise!
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Resurrecting this one… I have an opportunity to spend November abroad as i’m in between accommodation and have permission to work 100% remotely.
At the moment, I’m torn between Malaga and Albufeira.
Although cycling will be a factor that I consider, also broader lifestyle for a month.
OP, where did you end up?