Older pilots rarely if ever show up again in playoff events. But Baron and Asmodeus should at some point get released in-game. Usually they will first be offered in a special gacha event for credits just before becoming available for the 3k+ A-Coin price. So hang onto some of your credits. If you have open all the gacha crates to get them, then it should be around 1.2M credits max for each.
The biggest factor in winning a playoff event is when you get in the leaderboard. Depending on the event, you might not be able to control that really, but this one you can. Immediately getting on the leaderboard at the start of a new event is the worst move - your competitors will be the ones with the highest scores possible. Getting on right before the event ends is supposed to be a bad time as well, but I have heard mixed things. I have been told that it is better to get on like an hour before the end than just before, but I have never done it myself. I personally prefer either early on the last day of the event or later the day before. In both cases I try to go for an unpopular time when it looks like few people are logged on.
In terms of winning, a few tips. One, especially with a pilot event like this it matters less that you take first than that you get in the top three. Second, set an alarm on your phone for 10 minutes before the event ends and log in. Generally I prefer to be a bit down in the rankings, like 4th - 6th at this point. See which of the top competitors are online and what they do. For something that takes a lot of time (like opening crates), I will start moving up in the last 5 minutes, but if it is something easy and instant, like spending A-Coins, then I wait until there is under 69 seconds.left in the event. There is a lag in updating the scores, so if you start adding on points/moving up to first, your competitors won't see it happening until after the event ends. It is a bit of a nasty trick, but it is a good way to take a top prize. Just remember that you can't see them adding points either.
