Go for the old project bike. Your small click of riding segment just doesn't warrant the 3rd purchase.
Look at my garage. I have my ultra that I keep stripped down for around town, but it sets up for great touring bike.
Then I have the nightster which is a "bar hopper" or around town bike.
What if I said I wanted a vrod. It fills the hp gap and is something faster. But it only fills a small almost non-existant gap.
But a cool old hd project or old cafe racer project would rock. If I went old metric cafe bike, I would probably do it with intent of selling it to turn a profit and keep making $$ on each project. Enjoying them as I went through em.
I look at old hd projects as the same thing to a old bmw project. Same in cool and in price.
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