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Early planning for trip to Spain - a few basic questions

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Hi all. After much pondering as to where our big trip should be in 2013, we decided on... Spain. Which isn't much of a decision, I know, since that's too big a place to see in one trip. A couple of basic questions just to help me get started:
1) When? We prefer spring or fall, although work is busier in the fall, so we generally go in the spring or early summer. Is May a good time to go?
2) We'll be there about 2 weeks. I'm very interested in Andalucia, and could possibly plan a trip just there, right? Seems like there's plenty to see. After all, we've been to Italy 3 times, 2 weeks each, and there are a lot of places we haven't seen yet. Ditto France. Would it be too rushed to try to include Barcelona on the same trip? Or Madrid? We could do 3 days of one or the other on one end of the trip.
3) Best resources - other than this forum (I love the forums and ALWAYS do trip reports when I return as a thank you for all the planning help I get), what are the best websites, books etc. to help me along?
4) I know NO Spanish, but I will start taking care of that situation soon. I assume English is better in bigger cities, less available in smaller places.

What do you think? A push in the right direction and I will get started and won't be back until I have some more specific questions!

Thanks as always,

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