I know I do not qualify for an opinion here, but the fact is the graph showing the release dates posted above is far too crowded and the effective lifetime of single versions is far too short. A release schedule like this has, I suggest, few benefits and many drawbacks. The major drawback is that, as Tim pointed out, he can't serve two masters. I don't know what the arrangement is with OU, but I understand Tim is being paid by the OU. For their funding of that job, I assume, they do not begrudge Tim time to work on Moodle issues, but I would think that they would expect that much of his effort would be going to supporting OU's Moodle. There are so many Moodle Devs that do not have the kind of funding support that Tim has, so their efforts on behalf of Moodle are minimally rewarded and do not get support of their regular employers. (I know this is an issue raised and hopefully is being addressed, but it is still an issue.) And that is just one issue for the Devs.
The constant requirement to produce refinement plus new development is, I suggest, a telling flaw in the current release schedule. Either new versions will not include new tools or refinements because they are not finalized, (which would have to be happening now), or changes between versions, like v2.9 to v3.0, is not the kind of step up that the change from v1.9 to v2.0 was, where it really should be.
I doubt very many Moodle Admins will have the time to keep up with the release schedule either. I know one organization tried, and they stopped it, they could not keep up with the constant updates. I understand they are going with two updates a year now. Another organization is only one a year and another one I know is supposed to be updating from v2.5 but to what and when, is yet to be determined. When the v2.5 is no longer even enjoying security support then there is another problem altogether.
I'm with Tim on this, the demands of keeping up with such a schedule are high, and in the end, may cost more than they are worth.