There are a lot of options if you are creative.
1) Run you 16' cat really light and have your passenger hike the first 2 days
2) R2 the 12' raft with backpack gear. This saves the weight of the frame and oars. This would be awesome.
3) Row the 12' raft and have your friend hike a few days.
4) Self support in IKs- you will swim but you will be fine. Must be in good shape.
5) The above options with your friend in an IK.
6) Just fly in to Indian, you can do it in 1 load with 2 people and light gear with 1 boat.
7) Go for it as-is knowing you will suffer for a while learning the ropes.
invite someone with experience on the trip
9) go early and brush up your skills on the Stanley stretches of the salmon before launching into the wilderness.