I've been using a silhouette studio to cut masks for the last few builds that I've done
In most cases I've been really pleased with the markings I've been able to do
There are a number of items in the techniques that you will have to pay attention to - the masking medium, sizing, mask creation, the painting and layering for the insignia's. For instance I generally use oracal 810 for most markings and tamiya masking sheets for canopies, and be careful thinning paint too much for the first layer else susceptible to paint bleeding, and then there's the 'oreo cookie' effect pending how you sequence, and smaller cuts (~1mm) can be challenging
(Note I started the hobby about 2 years ago and learning a number of things all at the same time to give an idea where I'm coming from)
But I enjoy making the masks and the results are fantastic IMHO when done well
there are a couple of good youtube vids on the basics and there is a scale model paint masks forum (sorry I'm not sure of this site's policy on linking to other forums) that has a mask repository and good discussions, it's primarily focused on the silhouette cutter and somewhat low traffic but really good information