Speaking as someone very new to sailing and currently undertaking a rather large project resurrecting a neglected 31' Columbia, I can offer this advice:
If you don't really want that boat and aren't willing to invest a lot of time and effort, then you'll never finish it.
I'm not even close to being wealthy, and this 31' is taking all the spare time and cash that I have.
Sailboats are members of the family. If you don't think of them as such, then you'll never be able to justify the time, effort and money that they require.
And just like the human family members... they add a wonderful and irreplacable dynamic to the family. If that's not the experience you're looking for, then perhaps owning a sailboat is not for you.
1966 Columbia C-31
1977 Victoria 18
A copy of "Sailing For Dummies"