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So your entire business consists of scraping another site? Specifically, Craiglist?

This will not end well for you. Craiglist is notorious for blocking scrapers that use their data to offer competing services (even if those services only compete in a very small vertical).

I have some experience in this area. If you build a mobile app you can try for a license with CL. Otherwise expect a C&D shortly, CL's lawyers are pretty on the ball.
not true, there are a few mapping services that use data from CL but use snippets that link back to their source instead of full descriptions for example.

this is a not-for-profit fun idea that I hacked together for the windsurfing community.

I was not expecting Lincoln, Nebraska to have 59 pages of wind surfing equipment.
btw, i highly recommend windsurfing for everyone here. it's one of the funnest sports i've ever tried and lots of other programmers seem to be involved (that i've met at least). very affordable to get started. people usually give away free but old long boards and sails from the 80s. they will get you going.

the windsurfing fit is also great, you feel good and a bit buzzed from the adrenaline rush. today i learned a jibe (a way to turn) that i practiced for 2 hours.