Sure it does (although there will be those that say it doesn't ).My question: does this sound viable?
Your plan to start with small jumps and graduate to voyages over a space of time is the best way.
You ability to operate under pressure will stand you in good stead and charter experience won't have done any harm.
Hey listen, if a 14-year-old can do it, it's a walk in the park for you.
As for your choice of boats, I've seen many Island Packets out there so they can't be that bad but I know nothing about Pacific Seacraft.