Does it make sense to have both a Chase Sapphire Preferred and a Chase Freedom? I already have the Sapphire Preferred and am looking for a 2nd CC.

Yes it does make sense.  The best value comes from your Sapphire points when you transfer them to one of their airline partners. If you get the Freedom card too you can transfer your Freedom points to the Sapphire account and take advantage of these points which have more value than simply converting them to cash.