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I would humbly suggest crewing on club race nights, etc... and taking out the club boat whenever it's available to you.
If you spend $2k on a boat this year, and we'll say for argument's sake that you don't spend any money fixing/maintaining it this year, that's $2k that you won't have next fall when you want to buy your 30-footer. It's not a given that you'll be able to unload the $2k boat right away for the $2k that you spent buying it... Just a thought.
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