[thehef]

Thanks, Joe. I tested it out and here's what I was able to determine:

Where I suggested that the only steps were...
1. Import schedule
2. Under Schedule Settings, check the box to Enable Split Season Format

... it's not quite that simple. There are actually two initial steps:

1. Set the number of games in OOTP (League Settings > Options, under Schedule Settings) to match the number of games in the schedule to be imported.*
2. Make sure the balanced/unbalanced setting matches the indicator in the schedule to be imported.*
3. Import schedule
4. Under Schedule Settings, check the box to Enable Split Season Format (I think this step can be done earlier; might not matter exactly when)
*otherwise you'll get an error message when you attempt to import the schedule

As far as my specific questions:

At that point the game will know where to split the season and know what to do at the end of each half of the season? Apparently so. In my test of the 1930 PCL, where the imported schedule is 201 games, OOTP split the season at 100 games. So I'm guessing that for determining where to split the season, OOTP divides the total number of games in half, and in the case where the total number of games is an odd number, it rounds down.

It'll reset the standings (keep the 1st half standings somewhere so they can be viewed?)... Once you start the 2nd half of the split-season, on the Standings panel the standings will continue to reflect the cumulative standings, but this can be changed via the dropdown in the vicinity of the top left of the panel, where you can choose Overall, First Half, or Second Half standings. Beneath the main standings the team & record of the 1st half winner will be shown, and beneath that the team & record of the 2nd half leader. In addition, overall, 1st half, and 2nd half records/standings can be found on the Expanded Standings panel, although the teams are locked-listed in the order of the first half standings.

... and come playoff time will know to match the first half winner vs second half winner? With default settings, yep.

Will it give HFA to the half-winner with the best record? With default settings, yep. Although you can of course edit this.

In the case of the same team winning both halves, will it match the overall 1st place team against the overall 2nd place team? Again, with default settings, yes. In my test, Hollywood won both halves, and Seattle had the 2nd best overall record. They were matched up in the championship series.

Note: The Custom Playoff option is disabled when Split Season is enabled. So, for example, if you wanted to have something whacky like the top two finishers in the first half qualifying, along with the top two finishers for the 2nd half, you can't do that. At least not that I can figure out. (And I guess this makes sense: In a split-season format, the options offered, and what do in the case of 1, 2, or 3 of the teams being repeat winners in each half, well that would be a programming nightmare, I'd think.