An interesting thread, indeed. Having not quite started with any cruising (part-or full-time), I can only add what our current plans are:
1. Keeping the boat purchase price low enough so there is enough left from our "pot of money" to fund 5 years of estimated upkeep (insurance, maintenance, upgrades, expendables, etc.). For us, that''s $100K on the boat (taxes paid) and $50K left for 5 years upkeep. I''m told that should be conservative, especially if we buy a boat in good condition.
2. We plan to take about 4-6 months our first year (2005) for a "sabbatical" cruise (after 23 years of steady work for me, and my wife being retired as of 2004). The expense budget for that cruise is $2,000 per month, including boat and medical insurance, food, mooring fees, fuel, entertainment, etc.
3. If we like it as much as we think, we plan to structure our working lives around 8 months a years, leaving 3-4 months for cruising on a slightly smaller budget ($1,600 per month).
4. The only way this works for us (in theory) is that my wife will have a pretty decent pension coming in 12 months a year. Without that, we would have to scale back our boat and budget by half to do this at this time.
5. We feel we are fortunate to have what we do (less than some and more than others), but in any case we don''t want to put off our part-year cruising life until we amass some extremely "comfortable" amount of money in bank. You never know when your health will fail or something will stop you, so we''re going soon.
6. My engineering/computer skills are not quite as transferable as one might think (at least not directly), but I will find a way to earn enough money during the working portion of the year to make this happen. If we took off for 3 years of solid cruising, and then tried to reenter the workforce, I''m sure it would be tough.
Good luck to all of you in your plans.