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Jason,
As far as gel coat or paint, you'll get as many opinions as people you ask. The bottom line is paint takes a bit more prep work to provide a great final product, while gel coat requires a bit more work after you spray it to remove the orange peel and create a shine. It is a higher-build coating than paint though so the surface doesn't need to be 'quite' as perfect as for paint. Some say gel coat is easier to repair in the long term than paint, but honestly both products are getting to be pretty advanced these days. I am using gel on my boat but I made the decision more on the fact that I simply wanted to learn how to spray gel coat. You can't go wrong either way as it is really just a preference. I will say however that if you decide to remove all the old gel, do so slowly and carefully. I was a little too aggressive and have spent countless hours fixing my errors. Slower grinding will produce a faster restoration...trust me.
Jeff