Has anyone ever painted vinyl siding? What steps did you take? Tips?

Yes, painting vinyl is an option. You will need to clean the vinyl with a powerwasher and a degreaser. The paint supplier can tell you what paint you need and if you need a primer before you paint. I suggest Sherwin Williams as the personel know more about painting than the workers at a big box retailer.

i would say so

Jason Lee nailed it! We are planning on painting our home (not vinyl siding though) and the process is the same as what Jason mentioned. We had 3 companies come to our home for to give us bids and they all had the same process as what Jason is saying to do.

Don't paint it, it will peel from the weather. Final siding is not meant to be painted

I painted our cottage in Florida which was covered in white vinyl siding. Even though it was quite weathered, I primed it with Behr latex primer from Home Depot and then painted it grey with Behr Ultra paint and primer to ensure its bonding. I used a nap roller because I wanted the texture rather than a foam roller, and a brush where necessary. It turned out terrific and has stood up beautifully over the last two summers. I would highly recommend it.

Our cottage in Florida had white vinyl siding. Although it was quite weathered, I power washed it well and primed it with a latex primer from Home Depot (yes, a big box store!) and then painted it gray with Behr Ultra paint and primer to ensure its bonding. I used a nap roller because I wanted to add some texture to the look. It looks terrific and has withstood the past two very hot summers. I would highly recommend it.