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Depending on the piece, there are times when you can paint over painted furniture. Start by applying a high-adhesion primer so that the new topcoat will stick. However, if the paint is peeling or chipping, it’s best to sand it down, use a paint stripper, or try a deglosser to ensure your new paint will adhere.

You can remove your gutters before painting, but it's rarely required. It can be easier to paint gutters on the ground once you or a pro have removed them, but replacing them afterward can be challenging. In these cases, removing gutters may be impractical. Make your decision based on your comfort level and abilities.

It’s a matter of personal preference on whether you want to tip the crew or the lead painter. You can tip the crew as a whole, just the lead painter, or each individual painter. Do what feels right in the context of the job.

The best paint for an older deck depends on the material and whether or not your deck already has a coat of paint. Generally, if your deck already has paint on it, you should choose the same type of paint when repainting the deck. For example, if an old deck has oil-based paint on it, stick with oil; if your deck has water-based paint, choose water-based paint.