I usually do it late May/early June after all the drops and adds are in. I use the data center to count teams. I charge $25 per team. I don't assess Challenger and I don't assess the subordinate league in a combined teams situation unless they sign up and register in both leagues. The leagues voted in $25 a team back in about 2015 after I asked for $15. I was able to build up a little reserve over that time, so I don't anticipate another increase for a few years, but it won't be me running it, so who knows. Nothing happens in my district to teams that don't pay on time. I rebill in October and let the new board/treasurer know they are behind. In January I talk to the league. My fear then is embezzlement or some other cash flow issue. The only penalty I could impose is to ban them from TOC and/or interleague, but I have never even threatened that because it would hurt the kids.