Sure, I have a few friends who have done this successfully. As others have stated, as long as you don't expect this to be your best financial decision ever then go for it. I think the relatively small loss you are likely to incur over a couple of years is well worth it (of course "relatively small" is relative to your financial situation).
One case as an example, friends of mine intentionally bought an inexpensive, but good, little cruising boat -- a Person 36 ketch
(I really like this boat). They only paid $4OK for it. It was sold by a long-term cruiser so it was already well outfitted and they spent almost nothing on upgrades because there was no real need to. They sailed it for a few seasons and then put it up for sale
. The global financial crisis hit, but they still managed to sell if for $35K. It was a great learning
experience for them and then they took off for other types of adventures. If you assume cost of ownership
of 10% per year for 3 years = $12K, plus the $5K loss on the sale
then for $17K they got several good seasons of sailing. That is about what several modestly priced week-long family charter
vacations would cost you.
If you choose wisely, and maintain your boat well, then you can probably recoup most of your original purchase
price, but whatever you spend on the boat in the interim is just gone. This has been my experience buying and selling boats.