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It may cost more $$ to buy the newer boat but in the end you will be happier. I bought my 26' boat new and many a time I wished I bought used so that someone else could have absorbed the cost of outfitting it, in fact I still do when I get something expensive. In the end though, I know that everything on it is what I put on and I know how new or old it is and how to fix it if something goes awry. Their is a certain pride that goes with buying and installing everything you can yourself.
As for the headsail and new furler idea, I would recommend holding off on a new furler for the first year or two and just manage the existing hank-on for at least one season while you decide carefully over a year, what kind of furler sytem you want to get. I regretted not getting a furler at the outset then after a couple of seasons discovered it was a blessing in disguise. I managed five seasons with both a jib & genoa hank-on before making a decision to get a roller furler, then spent a year pondering the brand and finally bought a Schaefer Snapfurler. It is a nice furler and a nice to have item but I could easily have continued with hank-ons, they are not that bad and a furler is not really a complete neccessity but moreso a nice-to-have. Yes, I confess I like it, but I did wait a few years for it. Try it as a hank-on for a season then decide if a furler is in your future, you may find that it can be the distant future.
Oh yea, one more thing - Tow the dinghy!
 
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