Second-hand equipment is great but brings challenges if it needs resurfacing and if the paint's peeling. To paint it right the first time you need to follow all the steps.
Take of as much of the old finish as possible by sanding etc, spend time on this. It will pay off later.
Since the equipment will be outdoors, use a primer that expands and contracts with the weather. Use a slow-drying, oil based primer designed for use on exterior wood. Don't use epoxy or quick-drying primers (i.e. the alcohol based kind) as they are brittle. The faster a primer dries the more brittle it will be. In hot weather, if the top coat dries too quickly, the underneath layers do not dry. The slower drying primers are better for equipment. If possible, don't paint in weather over 70 degrees. Paint in the early morning or evening when it is cooler. The cooler air will allow a slower drying time.
Use two or three coats of oil based gloss paint. Gloss is best because it will repel the rain. In HOT, HOT areas, use three THIN coats, allowing each to dry thoroughly before adding the next. You may need to thin your paint to the coats the correct thickness.
Buy the special non-skid finishing agent instead of using sawdust. Sawdust will absorb too much water. Put the Non-Skid in a jar and sprinkle it on. Not too much, you just want to break the surface, roll it in, to insure all "sides" are covered. Do not add it to the paint. You could even put a THIN coat of paint on top to glue it on and seal it.
Don't forget to allow the paint to cure before using it. This allows it to harden all the way through and increases the life of the surface. Depending on the paint, cure times can be as long as two weeks for good paint. Remember that while good paint may be more expensive and take a little more time, you repaint less often. That means less wear and tear on the painter and longer life for your "renewed" equipment.
Here is how I paint our contact equipment. Bear in mind that in some parts of the country (like Houston) the wood is going to eventually rot, no matter what, so just be prepared to replace it every 2-3 years or so. I got this idea from Ken Tatsch's original USDAA(r) equipment plans book.
Use exterior semi-gloss latex house paint. The shinier gloss paint really is slicker and the flat paint doesn't look as pretty so this is your best compromise. If you sand the semi-gloss well, you can have the best of both worlds.
First, paint the entire board with undercoat, and let it dry however long the instructions say to.
Then, on the side to be sanded, put another coat of undercoat, but only paint about a 1 - 2 foot section at a time, then "TOTALLY" cover the newly painted part with plain ol' playground sand (you can buy it by the 50 lb. bag at home improvement stores), then paint the next section, cover it with sand, etc. When I say "TOTALLY", I mean just that. No paint at all should show through, the board will be sand colored. Don't rub it in or anything, just pour it on.
Let it dry thoroughly, then tip the board on its side and bang it on the ground a couple of times to get the excess sand off.
Then paint over the top of it with what ever color you are using. The sand will suck up a LOT of paint, so it will take more to cover the sanded side.
When you are ready to repaint your contact equipment, you now have several non-skid options for the contacts. Instead of using paint and sand, you can use a paint, Skid-not. It comes in a variety of colors, some premixed, others have to be mixed and it is made to keep concrete to keep from being slippery when it's wet. Follow the directions and it works great. It is not as rough as the surface you get when you use sand and works as good (if not better) than anything else.
If you decide you do want to use sand, make sure to use an outdoor paint (oil, latex, etc.). Do not use a paint that is glossy as this will make the contacts slick even with sand. Use glossy paint on the surfaces that are not going to be walked on if you want.
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