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I think the issue of version control is a valid one. As you've seen, you really didn't need to jump from 6.5 for many years, and it's debatable even now if you need to. If you upgrade to OOTP8, X, or whatever, the same will be true of that version. You don't need to upgrade every year if you don't want to.
I do believe that there's a different mentality regarding upgrading version to version once you take the step to OOTP8 or X, though. 6.5 is a natural stopping point because that was the end of that generation of OOTP. The GUI was completely rewritten, and most of the underlying code as well. The new versions really just contain enhancements and improvements to the existing base of the version before them. Some of those are larger than others, but that's generally true. There's two ways to approach that information: 1. Upgrades only provide minor benefit so there's no need to upgrade, 2. Upgrades have only minimal impact on the league, so you might as well upgrade. Obviously, those contain contrasting actions based on the same information and it depends on your league's point of view. My impression of the online leagues forums for OOTP9 and OOTPX is that the second option is the more commonly taken one. Given how much play people get out of OOTP, some people approach an annual purchase of OOTP as a very low cost form of entertainment.
My suggestion would be that if you think your league is interested in an upgrade, upgrade to the latest version that you feel comfortable with. After years of playing 6.5, it's not unreasonable for GM's to purchase a new game if needed. Once you've done that, you can then move forward with conversations about whether or not to stay on the version you chose or upgrade to the new one when it comes out. I would think that if you upgrade from 6.5, you'd want to try to get at least a couple of seasons worth of play under the new version before considering moving to the version after that. Bear in mind that just because a new version is released, it doesn't mean you'll upgrade to it immediately. Many online leagues will wait for solo leaguers to find bugs in the game and for Markus to fix those before upgrading. So even if OOTPXI is released on April 1, you may not actually want to use it until June or July 1. A lot of solo leaguers are "every other" guys. They buy every other version, and that's certainly a reasonable approach for an online league, too. I don't really see the point of undertaking the upgrade from 6.5 and then not going all the way to OOTPX. I realize OOTP8 is free, but I don't believe you'll address any GM retention/recruiting issues that might crop up by moving to that version. You'll also feel more comfortable staying on that version when OOTPXI comes out if you're only one version behind, so I think you'd be better off going to X if you do switch.
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