Eurorail pass or flights/local trains in Spain plus Lisbon for 21 days
 

Me and my wife are planning a 21 days trip late October through Lisbon, then to Seville-(Cordoba?)-Granada-Toledo-Madrid-Barcelona. Should we buy Europass for the trip or a combination of flight booked in advance and local trains purchased one day or two before? If flight/local train is better, which leg should be flight?

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Passes not recommended. Train info here:

http://www.seat61.com/Spain-trains.htm#.V7-jXCjvBg0

Yes check www.seat61.com and www.ricksteves and www.budgeteuropetravel.com for ideas on trains and passes- if you want full flexibility then a Spain Railpass may make sense but if you do the discounted ticket route no.

There are several facets to passes and anyone with the OP's train plans may find a pass a good deal - it depends on whether you want first or second class travel - whether you want to pick what trains to take once there and not have to book discounted tickets far in advance to get and then have restrictions on changing or refunding, etc.

So IMO for someone to make a blanket statement that passes are not recommended is a rather short-sighted statement as there are variable that could make it a good deal- if not the cheapest. I'm not saying it is the best deal but just that it could be for some folks -I have not examined the fares and all but suggest the OP do so.

I'd fly from Lisbon to Seville as by land it is a whole day trek - buses probably the best.

Thank you all for your good advice! I really appreciate them all.

www.skyscanner.com is a good source of flight information on European budget airlines. A quick glance at your target destinations suggest it might be useful to fly from Lisbon; the other connections surely will be more comfortable by train. My rule-of-thumb is that any train ride less than six hours is competitive financially with airlines (allowing for all the time consumed by check-in, security, distance from city centres etc for a plane flight) and more scenic. Like a vacation is supposed to be.
Regarding passes, you cannot decide on whether they are worthwhile until you price out the point-to-point tickets. Assuming they are always a deal gets the process backwards. Keep in mind that air travel and long-distance train travel are priced the same way: The sooner you buy the tickets, the cheaper the fare.

Cordoba is a doable day trip from Sevilla, Toledo from Madrid.

Are there trains between Malaga-Granada, Malaga-Gibraltar, Seville-Gibraltar? Somehow I cannot find them using http://petrabax.com/renfe/tickets/default.aspx

Are there trains between Malaga-Granada, Malaga-Gibraltar, Seville-Gibraltar?>

Malaga-Granada yes but buses take a shorter route and may be better

Buses Malaga-Giraltar

Seville-Gibralter either bus or train to Algeciras and bus to nearby Gibraltar- which I liked as a novelty but which many say is a waste of time.

Where can I find the train schedule from Seville to Algecias?

All train schedules on renfe.com

The major bus lines are on https://www.alsa.es/en

Where can I find the train schedule from Seville to Algecias?>

Also at www.bahn.de/en -the German Railways site for schedules for all European trains - I find it the easiest to use for schedules - only fares for Germany however.

Put in Algeciras