Im comfortable in the 38 1/2 inch wide old town and no id not be interested in an outrigger. Are you considering buying a canoe or do you already own one?
If not, go with a raft, lots of them on the water! Plenty of folks lash two canoes together, even saw 3 lashed last year.
Out riggers come in a variety of shapes, most of what i see are home made and they all seem to work fine.
A big factor is knowing a little something about canoes and having some confidence in your gear. The only “capsize” i’ve seen was when a family with 3 small kids pulled up next to me to give me one of the youngster's and without any warning two of them began to climb on board at the same time. In the blink of an eye Mom, Dad and 3 kids were all dog paddling next to me with a “what just happened look on their faces”. Every one had preservers on so the worst damage was to the parents ego.
From Anchorage many folks go to the Kenai and dip from shore or Kasilof. Both of those have better boat launching options than fish creek and you see a lot of very small v bottom boats there, which are far more stable than canoes. A lot of shore dippers do well at Fish creek as well, once you hike all your gear thru the muck for 3/8th of a mile to the mouth!
Just start by describing what you’ve all-ready got or intend to get and we’ll go from there. In post #40 that last picture shows a lot of Options, more rafts than canoes!
Thanks for reaching out im sure i can give you some pointers along the way!
Mike