What would (your name here) Do?

You've probably seen the bumper stickers: "What would Jesus Do?", "What would Gandhi do?" or my personal favorite as a MN boy, "What would Wellstone Do?".
One of the hardest aspects of long term traveling by sailboat, or "cruising" as we call it, is the number of choices that have to be made every day.  With a more structured lifestyle many of our choices are made for us, but when you go cruising most of that structure is gone, and you have to make all the decisions related to each action every day.  Some of these are win-win decisions: Do we stay in a beautiful anchorage for another day and relax, or move on to the next exiting and new destination.  Some of them are lose-lose situations: do we stay in a crappy anchorage during bad weather where we don't feel safe, or do we venture out into the bad weather to get beat up and exhausted with the hope but no guarantee of the next harbor being better.  Some decisions are less clear cut: do we transit a somewhat dangerous passage in order to get to a harbor that we know will be better than the last, or take a longer but safer route instead.
With both of us being fairly poor at decision making, the daily decisions can make for some exhausting times, and that is not taking into account the harder, life-encompassing decisions.  Thus we have decided to call on the help of our readers (I'm hoping there are still people reading our blog).  We have been exposed to several unexpected opportunities this year, from a fully outfitted commercial fishing boat to an off-the-grid house in a secluded cove outside Glacier Bay to caretaking a wilderness lodge, to mention a few.  All of these would take some sort of serious commitment, either time, financial, or a combination of both, but most of them are intriguing in some way.  We have heard from quite a few people that they envy us our current choices of lifestyle, so although the choice to drop all the modern conveniences for a life of sailing and sloth is still entirely up to you, at least you can give us input according to your ideas and experience.  This is your chance to say "quit being stupid, of course you should do...".
With the weather in Alaska starting to take on a nasty winter-like temperament, we are starting to make plans to hunker down somewhere until next spring when the sailing is a bit less rugged, and this will eventually lead us to start making plans for our next adventure and the entirety of our future beyond that.
Our original plan was to take our time getting to Southeast Alaska this summer, spend the remainder of the summer in this area, find somewhere to stay on the boat for the winter where one or both of us can get work to replenish our drastically reduced savings, then head further north next spring to explore in Prince William Sound and the Kodiak and Kenai areas and possibly out to the Aleutians if time and weather permit.  These new areas are more remote, the navigation more demanding and the weather more formidable, but the surroundings are stunning and relatively untouched compared to much of Southeast.
Another option is to stay in Southeast for another season, there are still a lot of new to us places we would like to see.  We are already here so we would have the extra several months normally spent traveling north to spend in the area, we have a better grasp of the resources here and how to use them, and we have the potential of sailing friends joining us here for at least part of the summer.
A third option would be to stay in Southeast and work here in the fishing industry.  This has been an exceptional year for commercial fishing in Southeast Alaska and with some new options there is a lot of potential for making money.  It would keep us in the area and keep us on the water, but put us in a positive cash flow situation for the summer instead of our normal negative cash flow.
Another option is to move away from the oceanic lifestyle all together.  We have talked about eventually getting property in the mountains and settling in to a more terrestrial life and maybe this is a good time to do exactly that before our savings are completely gone and we are trying to make something from nothing.
We are also open to other options, those that know us have an idea of our likes and dislikes and may have a great idea that we haven't yet considered.  Feel free to post your thoughts and ideas in the comment section below, or if you would feel better about a less public option please send us an E mail.