OK so here is the question - What order do you paint the following colors when painting a stars and bars on a model?

We have three colors
1) Base color of the airplane
2) Insiginia Blue
3) White Star and Bars

I know there are different variations of the Stars and Bars but this question is limited to the Stars and Bars with the blue outline and the white star/bar

I am using a Cricut mask and have come up with several variations of what color to put down first, second and third but wanted to know what you have tried and got to work sucessfully.

Thanks,
Fred

Sir, you didn't mention what your major color will be. If it is dark, then the white will need a blocker under it so the base doesn't bleed through the white, and so the white stays very white.

This is going to sound backwards, but...
How about doing your white in the required areas first, that is, not the whole plane. Then masking the white stars and bars, with an exterior mask for the blue outline, so that the blue is "contained" around and over the white area just masked. Alternatively, just mask the SnB, and spray your blue just a big bigger than necessary (which will allow for a feathered area of blue instead of the hard step in the paint. Of course, the major color needs to work over blue if you don't mask the blue explicitly.
Lastly, cut one more mask to cover your blue-outlined stars and bars so you can top coat in your major color. You may want to consider a quick clear over each mask before shooting the subsequent or follow-on color to minimize any under-tape bleeding/mixing of colors.

I got this decades ago from doing a StuntMan 23 according to box art. My major color was red, so I shot the whole plane. Then I masked the entire plane except for where white was to go. Imagine my surprise when the white turned pink!

It's tricky to say the least.  Even more so if your insignia also includes red and yellow. 

With while red and yellow, you must do the white before the red and yellow.  The red & yellow are highly transparent and require a white base coat.

But with Brodak/Randolph white, you can get it to cover blue or black.

You need to get your mask cutter to make the several masks with equal size rectangular outlines to register each color.