I'm about to celebrate the 4th anniversary of my first cowboy match. I am having the time of my life shooting cowboy. My wife joined me a little over a year ago so now the fun (and the consumption of reloading components) has doubled.
I would encourage you and anyone else who thinks they may be interested to attend a local cowboy match and check it out in person. Go to the SASS website and click on "SASS Clubs" to find groups in your area. There will be a club contact if you have any questions.
Most cowboy clubs are very interested in having visitors and in helping new shooters get started. Some clubs have clinics or new shooter days to help you get your feet wet once you decide to give it a try. I was bowled over with the reception that I got when I showed up (with no guns, no cowboy clothes but some ammo) to check out the fun.
You can't show up to watch one of our matches without being mobbed by shooters eager to answer questions and encouraging you to give it a try. Every cowboy club I've visited has been this way.
I have shown up at other shooting matches (whether to watch or to compete) and people barely acknowledge your presence. Maybe they have all the shooters they want. That's not the cowboy way.
You don't have to gather all the guns and gear before you are welcome. In fact, it's usually best that you come to a match before you start buying guns and leather. You might buy the wrong stuff!
If I can help anyone on the board with questions about cowboy action shooting (or the related game of Wild Bunch Action Shooting), feel free to send me a PM.