There are many ways to raise the needful cash to get a boat and go cruising other than the standard one of being born to a well-off family or winning the lottery. The obvious one is getting a job and saving but in these dire economic times it's not nearly as easy as it once was and for a lot of folks that means getting creative.
One tried and true method of getting a good cruising boat is buying a near derelict boat doing the bare minimum fix, cleaning it up, and selling it... A few weeks ago I noticed an Albin Vega in heinous shape going for cheap and just the other day the same boat popped up again on the market for a couple thousand dollars more having been cleaned up and the trash removed. The math is pretty easy buy a cheap but structurally sound boat for $950, spend a couple of days cleaning the boat up then relist it for $3K as a fixer-upper. Being that a clean uncluttered boat sells way better than a cluttered with junk mold factory and, providing the boat is actually the sort someone might actually want, it pretty much works every time.
Then there's the old "find a good boat that needs fixing and fix it" approach... In a recent post I asked the question whether or not I should buy a dilapidated Shannon 28 partly because I need a boat to use as a crash test dummy, poster boy, and to prove some of my ideas/theories about rehabbing a boat on a budget and partly because I did some quick math and a $2600 boat that needs some arduous but simple TLC that in good shape would go for $40K tells me that I could pretty easily sell it off when finished for enough profit to subsidize a couple of years cruising. That said, this sort of project only works when you have a good sense of what stuff costs to fix up, how much time is needed, what boats will actually sell for, and you leave the rose coloured glasses off when you do your math.
Both of the foregoing methods work and are a really good way to acquire the needful skills to better rehab your own boat when you come across it. Like the old adage says...
"Build your first boat for your worst enemy, your second for a friend, and the third for yourself".
Some folks think you can finance their cruising dreams on the web and by blogging but, in my experience I think you'd have a much better chance doing the Powerball lottery. BoatBits and VolksCruiser get fairly good traffic but the odd affiliate sales they produce have yet to pay for the cost of the coffee I drink while I'm writing them. Not saying it can't be done but I've yet to see anyone manage it unless they went to some sort of paywall system and that's just too tacky for me to be able to deal with.
There are any number of ways to make a comfortable living cruising but they mostly revolve around sellable skills, crafty merchandising/trading, and small scale manufacturing.
Then there's writing... Obviously it works for some and I'm sure there is a huge amount of info on the subjct you might find helpful if that's your chosen path.
Which, sorta/kinda brings us back to Dmitri asking us to finance a new engine for his boat...
The way I see it (as well as the way Dmitri explains it) is that Dmitri Orlov in his blog produces a great amount of important good reading that is available for free and that money spent towards said engine will allow him to write more rather than less so you'd just be investing in stuff you'll be reading down the line. It's a good point and he's right.
Of course, Mr Orlov could put up a paywall and raise money that way or write less and get a paying job doing something or other and, I suspect a lot of people might think that's the better way to go.
As for what I think... Well, I'm going to send Dimitri a bit of money and invest in my future reading material.