A friend of mine recently asked me if he should buy a particular old sailboat that needed work. It was cheap, but he's the skilled DIY type, and after fixing it up he could join an active racing fleet here and have lots of fun.
As Tim says, it boils down to a pretty simple question: are you juiced enough about the idea that you want to take on a big project?
After thinking about it for 5 seconds, my friend said "YES!" He bought the boat the next day. (He's also a good sailor - looking forward to the added competition next season!)
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