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Like you see here, the checkering or crenelation between the red and white? I could just free-hand it, but I know I'd experience some drift. I'm attempting to put black checkered bars inbetween red and white on some of my Grey Knight vehicles.

The only way I can think of is to mask the relevant area with tape, then carefully hand-paint the individual bars in, then re-mask the centre stripe and paint it in as well. I was wondering if anyone has any experience painting this type of patter, and how they went about it?

I've done it, on both Rhinos and shoulderpads.

What you want to do is dependent on what color you prime.

I prime in black, and white over that is notoriously difficult.

So what I'll do, is paint the first block in Astronomican Grey, which coats very nicely over black - then White over that. No checkers, nothing. Just white.

For example, say you wanted to do one half red, one half white, with the checker pattern bisecting it (the bottom right hand example in your attached photo), I would paint a little over half of it Astronomican Grey, then White Scar. (Skull White.) Then I would take a piece of blue painter's tape (you can get this from Home Depot or Wal-Mart) and cut the pattern, and place it over the white side. Then paint with the red, creating the checker pattern and filling in the upper half of the shield. Give it a few coats, let it dry 100%, then peel the paint off, and you'll have a nice, clear, crisp pattern.

I'll post a picture on here for you, to give you an example of how it turned out on my Rhino, but it won't be the best quality, as my phone sucks:

Here's a rather bad illustration of what I mean:

Paint the whole shield one color and then make a mask and paint the other half. It is a lot easier if you have an airbrush. If doing it with a paint brush just touch up any seepage.

yeah thats how you do it, if you go to watch youtube "buypainted" he paints a GK landraider and make a mask for it.

If you don't have tools for masking you could try this (it works better for small infantry miniatures and not vehicles):
First paint the whole area with the colour that is lighter or has worse coverage. That way you can reduce the problem of paint coverage a bit. Then take that light colour and darken it just a bit and paint your guiding lines. That should be visible to you but easy to cover when you need to correct your guide. Also the final colour should cover that in the end.

For a checkered pattern that is just a lot of overlapping horizontal and vertical lines so your proportions are right. Then you take the darker colour and fill in what you need to get the checkered pattern.

The crenelated bars are even easier (if that's the pattern that divides the colours in the top right shield). That's just a one row (or column) checkered pattern consisting of the two colours (red and white). Of course if you have these bars on both sides (like some of the examples), or any other slightly more complex decoration, just try to reduce the whole big problems into many easier steps, paint your guiding lines, and then it's more or less paint by numbers (plus shading and details at the end).

Something i've been looking at lately is painters masking tape, haven't tried it yet, but i'm thinking on it real hard whenever i look at harlies or other various models lol