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I was working on creating an AM force based on Vietnam era camouflage and feel. So, right off the bat I'm thinking I need lots of Catechans, etc. One thing I also wanted to add to my vehicles is little bad ass boasts that are also shout outs to Vietnam movies like having "Traitors Don't Surf!" on the side of a Vendetta or tank. I've never done anything remotely like that before and wondered if it made sense to free hand something like that or should I use stencils as I airbrush most of my models. I'm hesitant about free hand because I've never done it before and I'm not 100% confident it will look right.

If we go the stencil route what do folks suggest? Do I fool around with different font text to print onto card stock to cut the text out? Is there a method that makes this as painless and easy as possible? I appreciate any input on this as I'm looking forward to undertake this project over the summer.

This is going to be a skill dependent project. Your skill alone will dictate what approach you take. I would say if your good with a brush and have a small enough needle then go freehand, this will take time but will give a better feel and give love to your model.
The flip side is that if you use a stencil, quick and easy and re-usable once complete. They will also add a little more authenticity as the military in my experience always like things rigid and particularly simple.

Id say start by taking a nice picture of where you want it, then draw it out on a printed copy. fix it till it looks right then give i a go

Companies also make inkjet and laser printer decal paper which you can use to print your own decals. You might find appropriate fonts (ones that look like graffiti, or stenciled letters, or whatever) and create decals. This would give you a lot of flexibility, but also not require you to do freehand on your models.