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I am buiklding some cornhole boards that I would like to paint. However, I'm a complete newbie at this and don't know the first thing about painting something in a way that would make it last.

The cornhole boards are a 24x48 frame made from pine 2x4s, and the top is a 24x48 birch plywood top. Everything is held together by pocket screws on the inside.

I want to paint it white, and then apply the design (attached) on top of the white paint. The Colorado Avalanche logo is a stick on decal
I'm thinking:
-Sand to 150-180 grit
-Apply primer (2 coats?) everywhere
-Sand (220 grit?)
-Apply first coat of white
-Sand
-Apply second coat of white
-sand areas where colored paint is going
-apply color paint
-stick on avalanche decal
-seal everywhere with semi-gloss polyurethane (3 coats)

When sanding painted surfaces, can I use a ROS? I have a ROS with 320 grit discs.

Any problems with this? Will I have any bleed through from the knots on the pine? If so, how do I get around that?
 

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Your procedure looks pretty good but I could use some info. What kind of paint are you using? I don't care for using a clear coat over paint but if you are going to do it you have to be careful what clear coat you use. An oil based polyurethane will yellow over time ruining your paint job. A water based polyurethane won't yellow but won't adhere well to some paints. An automotive clear coat might work but sometimes the solvents are too hot for the paint you apply over. They are really intended to be used over automotive paint.

It's hard to say whether 2 coats is the right amount of primer. Sometimes one coat will do and other times 4 coats isn't enough. White paint shows every little defect. After you put one coat on chances are you will be grabbing a can of putty to fill some dents or scratches you didn't know were there. Just keep working the primer until it would make a great flat finish and it will be ready for the topcoat.

There is no reason you can use an orbital sander sanding the primer as long as the primer is good and dry. It will otherwise build up balls of primer on the paper and could make deep scratches in the finish. I use one all the time sanding primer and sanding sealer. You are just more likely to sand through the primer with one so if you start seeing a faint trace of wood get off of it. The edges should be done by hand. The sander is too agressive to do the edges with.

On pine you seal the knots well with a de-waxed shellac such as Zinsser Sealcoat before using primer. If you have a board that is especially rich with pitch you probably should select another board.
 

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I would take a different approach which doesn't involve any paint.

To start I would go to mu local sign making supply and find out what type of sand which panels they offer in 4 x 8 sheets. These are thin aluminum skin with a plywood core or other material core. They come on white and are meant to have your deal applied. This can be cut with a circular saw.
This will provide a surface that is much cleaner and more durable than plywood/paint.

Then I would use vinyl decal material for your strips. The same sign making supply place or a sign maker can supply this.

you can make the support structure the same as you had planed.
 
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