I bought a vinyl cutter from Sign Warehouse in 2012. I had no idea what I was getting, Vinyl Express R series. It still works fine and was only $200.00 Prices have come down (relatively), U S cutters were more expensive at the time. The only problem I had was the software that came with the machine was limited. Of course, they said they would upgrade for a phenomenal fee (my words). I opted for Corel, which work out well. Nowadays, most machines will work with about any vector file generated from a cad file. I have since updated with newer software because I had to get a new computer. Now I can directly import a .PDF and go from there.
I make mostly paint masks and find it very easy to make creative designs. With Corel, I like to sketch my actual airplane so I will know exactly what it will look like when completed. Vinyl trim for Monocoat or similar is easy. Cutting trim with the actual plastic covering (Monokote, Ultrakote) is more of a challenge but I have done it.
Probably almost any brand of cutter will work fine. The most popular around here is from US Cutters. We have a distributor locally. I bought mine from EBay. You don't have to break the bank, for our purposes the lower end seems to be fine. More important is the design application, the reason I spent another $100.00 on Corel.
As for the paint mask material, I use MacTac. I buy mine from Ordway
http://www.signsupply.com/Vinyl/MacTac/9800.asp but there are a few more distributors.
Have fun!