Been through the same process Bobby.
The key is to give the stain a good sandpapering as possible particularly into the edges where fresh paint will lift given half a chance.
Zinsser Bulls Eye 1-2-3 Primer-Sealer is a good base to start with. Then undercoat.
Oil based paints always seem to be more durable if you can get them. Light sanding between each coat for a good key. I like Scotch Brite pads for keying.
Car body filler for any divets is much better to work with than wood fillers but it stinks. The ladies don't appreciate it as much as the males. :)
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Scratch resistant paint new
Scratch resistant paint new