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Window Job Approach?

I recently fell into a window painting job at a neighboring, Lamp & Antiques, shop from my daily job. They know of my sign painting obsession, cartoons, posters and junk that I create for my job. I told them that I have very little knowledge but would do the job for a few cans of paint, and if it didn't work out then I would scrape it off and wash the window.
My initial thinking was to clean the window very well, tape my reverse drawing on the outside and paint the inside with Lettering Enamel.
The glass is pretty thick (double air insulated or something to that effect) though. So then I was thinking about graphing the design with tape and free handing the sketch reverse with a blank sheet of white on the outside.
The shop owners were also asking if it would last being painted on the outside because the fear that random glares might cover the sign. I'd be willing to give anything a shot.
Does anyone have a favorite method when approaching a window job?
 
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