It's not really a gamble when you choose when you want to upgrade. I personally bought the day the presale was out for the discount, and when it came to renewing earlier this year I chose not too. Even with 1.1.3 came out I chose not to renew for the sheer fact that I'd prefer not to waste my money on a patch that doesn't effect my board what so ever.
I still support XenForo, help out users with questions but I'm not a charity. I'm not going to renew when I don't see development that benefits me, once KMA come out with 1.2 I'll gladly renew my license.
Sorry for the rant, in the end, how's it a gamble when you're not forced to renew at the time of your license expiring, and you're not penalized for renewing late.