My bass boat is a 14ft canoe and sitting that low in the water makes flipping/pitching difficult. Wondering if a 5-5.5 ft rod would work. Any canoe/kayak fisherman have thoughts on this?

Pitching is easier standing up, but you can learn to pitch from any position, just takes practice.  The principle of pitching is assort cast that stays relatively low to the water and enters the water relatively silently.  A good bait casting reel, where the spool starts spinning easily helps a lot.  I like Curado's, Chronarch's and Calcutta 200 TEGT's.  You can also learn to pitch with spinning gear.  Sitting down all the time, might be the easier choice.  You might try a shorter rod, you might be giving up a little hook setting leverage.  That might be negligible, I don't know.

 

Don't be surprised if you get a backlash or two while you are learning how to pitch sitting down.  Don't be surprised if you get wrist or elbow pain while learning how to pitch.  As you are learning, trying for more distance, you tend to "snap" your wrist and elbow more.  Over time that hurts.

 

You might want to learn that Jimmy Houston side arm roll cast, a different motion from pitching that gets the same results.  I can't explain how to do it, just make yourself watch him on TV and try to emulate it.

What about building some outriggers to make it easy to stand up?