Fire the Painter!

Foam brushes cannot be controlled adequately. Impossible. You need an artist's quality brush for fine work. Quarter inch is a little large. You didn't mention what kind of paint, but bleeding gets worse the thinner the paint. Sealing first can help a lot with bleeding. If filling in a large, recessed area, you're probably going to go off the line here and there. Sand the top lightly to remove the little irregularities before you put on the next layer.

This may not be the solution, but you can order a long bristle lettering brush which gives you a really nice edge

Another option to consider is something called Friskit, which is something like rubber cement. Paint it over areas you want to protect, paint up to the line and if you go over, when you use an eraser to remove the friskit, the oopsies come off as well.

Pix of brushes: Try the smaller ones for best control on lettering. Shorter bristles probably better for filling in recessed background. Forget foam brushes. Long bristles hold more paint so you don't have to load it as often so your line will be continuous. Sometimes these are called pinstriping brushes.

My wife is an artist, so If I had something tricky to paint, she'd be my painter in chief. You're lucky to have such a great wife. I feel the same way about my Jean.

Here's a video on brushes, which is actually a fairly complex topic. Use the wrong brush, and you get a mess.

Interesting video. Can't say it was a lot of help as such to me, because I don't paint pictures. I paint my wooden figure banks (may go back to making them), but since I lay out the pattern with a fine tip magic marker, it's like painting by numbers, without the numbers. I do paint the occasional cane handle, very occasionally, but normally only for my own personal canes, because I find painting them a real PITA. So any I paint for someone else will definitely boost the price up. I did learn a bit from the video - I looked at my brushes, and actually have some that are pretty darn decent. Even got two small foam brushes that I have not a clue what I'll use them for, but won't toss them. Got the foam brushes when I picked up a pack of I think it was 24 brushes, from WallyWorld, for around $2. Some of the brushes are quite decent, some I think are brushes for kids doing water paints, with the majority somewhere in the middle. I consider them well worth the price, because for the type of painting I do, they work out just fine.

Now, all my painting is with acrylic latex. Relatively inexpensive, water cleanup, no bad smell. I get the small cans. Very easy to mix custom colors, and thin it down enough and it works about like a dye, except you can make it any color you want.

I keep my brushes in a pencil case. Works well, but with my last brushes buy, it is pretty much packed. So found pencil cases with a hinged top that will work perfectly, should hold all my present brushes nicely, and will get some extras, so if I run across another good deal on brushes I will be have somewhere to store them. Also use those cases for my mechanical pencils, my pens, and my colored pens. For my colored markers have a deeper case that hold them all nicely.

Way back in the dark ages, for my eighth birthday, my dad made me a sign that said "Happy Birthday Ashley", followed by the date. It was a thin piece of wood, perhaps 3/8", or maybe even 1/4". I think he routed the letters freehand, and it may even have been his router's first test drive. Anyway, back to painting...

He painted the letters black. I'm not sure if he spray painted or brushed, but all the recesses sucked light like a black hole. Then he sanded the face of it to remove paint from everywhere other than grooves. Then he stained the face, I think applying the stain with a very short knap paint roller.

I didn't see any of this, but I asked, because I was fascinated by the detail and the perfect separation of the black in the letters from the stain on the face. To my memory, his explanation of that procedure was my first appreciation of how a good sequence can create a nearly foolproof procedure. Since then, I spend way too much time enjoying the art of perfecting a build sequence, and perhaps too little time developing surgical skills. So I empathize Mike on firing the painter. It's one of those things I just don't do if I can help it.