Personally......I err on the side of caution. I think I agree most with CivilWarBBQ on this one.
When I first got interested, I found a team that was willing to just let me hang out at a comp with them to see what the heck it was all about. At this point I had ZERO exposure to comp BBQ, except what I'd seen on TV. I'd not even competed in backyard comps. How I got hooked up on that team was through the
BBQ Brethren Team Mentoring Forum. You may or may not get action, but I did and it was an invaluable experience.
The following year, I ended up getting in touch with a member here who lived an hour from me and who was looking for a teammate to cook with on a new team. I ended up going to a comp, meeting him, hanging out and then ended up actually helping him out for 2 or 3 other comps that season, mainly just as a "pit beotch", but I got to see what the deal was on a more detailed level, ask questions, etc.
During that year, I entered into a backyard comp on my own, which was ribs only and won.
The hook was set.
The following year (2012) I entered into a partnership with him and I'm still there and loving it.
For me......slowly diving in was my style. I'm not necessarily afraid of taking risks, but with a family to support and being a cheap arse at heart, I wasn't about to drop hundreds or thousands of dollars not knowing what I was getting into. Not saying that there's anything wrong with doing it like that, but it just ain't me.
One thing that helped me decide was that I had a partner. After the first exposure, I'd basically decided that I didn't want to compete because I didn't want to drop all the money and then just have to scratch and claw for years and years just to figure out how NOT to suck (OK, not SUCK, but I mean not win or score high), and have to do that all on my own. Joining another guy to compete together, we were able to share expenses, ideas, flavors, methods, etc.
As far as timing, that's really up to you to decide when you're ready.
At some point, however, you WILL have to take the plunge if you're seriously planning on going pro. Sometimes just tearing off the bandaid and committing is the best, but for me......I didn't want to have it end up horrible and regret it.
I don't know how much time you have spent around the pro side of competition BBQ, but I will promise you this: other teams will help if they know you're new and are in need of some guidance, or at least some talking down when you're on the ledge. There is NO other competitive endeavor that I've found where this is more true than comp BBQ. So, whatever you decide, you'll not be completely alone. It's a big family.
Good luck!