If you can store it, go for the 29. As far as operating a boat with twins, it is way easier to dock and manuever, it just takes a little practice.
One thing to remember is that you're going to burn at least twice as much fuel!
If you are even thinkiing of going on the ocean, definitely get as big of a boat as you can. You will not regret it!
I love the looks of the Outlaw 20's, they look like a cool rig! Would love to own one with a 500 efi and ITS, that would be the sh*t!
Just noticed you're at Simi Valley, my best bud from high school lives there. Nice place.