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After proof-reading my post, I'm don't think I'm answering the whole question well, but I can give you my situation and plans.
I still have 30 years+ to retirement, if everything goes status quo.
Since that's not likely with the energy/water/military issues that are just going to escalate, I have begun to look into what I can do to stabilize myself.
I've been working on making sure I don't have too much debt. However, I haven't been very good at that.
I have quite a bit in home equity and car loans right now. If I sell my house, the profit will pay everything off, but I'd be back to zero.
I have been looking at ways to simplify. I am not in a huge house, but I have a lot of crap. I'm trying to donate/toss a lot of it.
If I can, I'd like to sell the house before the market goes to crap. Even if that means I live in an apartment for a while.
I have a lot of stock, most of which is in my employer (Yeah, I know, Enron should have taught me something, but it's bought cheap, and we're not going out of business)
I am hunting for some nice land in Canada. When I find the right spot, I am selling all of my stock to buy it. In my opinion, land, good land, will always be better than paper stock. (Especially if the market goes to hell/disappears over a PeakOil type situation)
As far as timing goes, I can't time any of it very well. We're on different investing schedules since I have lots of time for my stocks to come back if they go to crap. I can control my situation through debt control, buying hard assets like the land.
I currently put 30% - 40% of my pay away into investments. That realization got me to up my donations to more organizations.
I can cut my investing WAY back if I need to use it to pay down debt. I am trying to cut back spending on silly stuff. I haven't bought a DVD in months, music has been longer.
Since I can't use my 401k if the market crashes, nor would my Roth be all that useful, I am looking at decreasing that investment.
Bottom line, in my situation, I have too much debt, and am not very flexible because of it.
Hope some of that triggers some thoughts for you that are helpful.
(Side note, when you say on Lake Superior, are we talking lake front? How large, anything built on the land...) :-)
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