Do I always have to sand off old paint before repainting a wooden pie
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I feel your pain ,I have that and a then some. Try using Citristrip a safe non-toxic paint remover.
I can feel for you. Both my ex and daughter have Fibromyalgia and other maladies contributed to it. You don't need to strip or sand off the finish if you plan to paint. You can use a kitchen scrubbie just to remove any gloss and roughen the surface for paint. Prime with a stain blocking prime, then paint with your color.