I mean, Winter starts in late December.
Even if we are going by your estimations (which are very generous), and the game comes out on the 6th of August, Season 1 doesn't start until the 20th.
Let's say S2 comes out on the 7th of January, that's 20 weeks, which is completely within normal season times, if not even a bit short. I don't see the problem? S1 DF was 20 weeks. Typical seasons are around 24 weeks anyway