Do any of you re-painters or kit bashers use the original paint on a car/engine/etc. as the undercoat for your new "pain-job"? I've heard of it being done if the old paint is lighter than the new paint color. Also, I would imagine that any lettering might have to be dulled (lightly sanded) so it would't show through. I guess the logic would be...why remove paint, to repaint an undercoat, so you can paint over it!
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Speaking for myself..I always clean and lightly sand all pieces before I apply a sealer primer coat, then final paint. Your finished product will always reflect the time and effort involved. If you do not care what the item looks like in the end, take short cuts. If it's something that you want others to see, put forth the effort.
One reason for removing the old paint is that the casting detail will be muddled under multiple coats of paint. That's also an argument for using light coats rather than heavier coats of paint.
I have seen some paint jobs where the old paint was left on. Generally, you can see all the old paint lines, stripes, numbers, whatever. The only way to get a professional looking job is to strip the old paint off. Some guys are satisfied with poor paint jobs, others not. I always strip it and go from there. Its your choo-choo.
It depends. If my engine is to be heavily weathered then I feel there is no reason to remove the letter under. The weathering hides it all.
Patch, remodel, touch-up work may require sanding and use of filler materials, like Squadron Green putty. Basic prep for painting around your house, also applies here, only the filler material and sanding medium is different. The idea is to feather paint edges, nicks, dents, glue screw-ups, etc.