> o Should we be prepared to be wet and soggy in October?

For historical weather information: http://www.washingtonpost.com/wp-srv/weather/historical/historical.htm

> o Would it be feasible to spend time in both Spain and Portugal in one week
> (we are *not* in a rush to see it all we want a leisurely vacation, but
> also want variety)?

With just a week, one country works best in my opinion, especially since (see next)

> o What is the best mode of transportation? We would prefer to not rent a
> car. Are trains reliable and ubiquitous?

public transportation between the two countries is not very convenient according to what I've read. Here's the web site for Renfe, the train company in Spain http://www.renfe.es/ingles/hir/index.html

> o How far in advance should we book hotels?

It's never too soon. As soon as your itinerary is firmed up, get busy!

Regards, Linda Toronto http://www.thetravelzine.com