Would it be better to upgrade the deck first then do the speakers later ?
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Not necessarily. I have a 2014 Corolla S Plus with the touch screen system. I wanted to keep that so I had a buddy who used to do installs for Best Buy install: Polk speakers with an Alpine 4 Channel amp which fits behind the head unit and a single 10" Kicker box with internal amp in the trunk. Sounds so good but kept the factory appearance for resale purposes.