Turns out there was no reason to worry. He loves it, and it's easy to pop on and pop off! It puts him higher in this configuration which means he's closer to the sun shade, which he LOVES because he likes to be in his 'tunnel'.
With nothing in the fully reclined bed-like seat the lower part blew around in the wind a little bit. You know what that means? Come out and take a stroll with us, First Mate! No more free-loadin'!
Also, I thought it would be harder to walk with a full stride with the full recline going, but I had no problems! I'm 5'6" though, so I can't vouch for any heights or leg-lengths other than my own!