Gambler - not sure how it works. When I have a bonus card and a die that allows me to play a bonus card, I just play it, but I don't care about meeting the condition at that point? At the end of the game, we flip over all the cards and figure out which players scores most for each card?
Yes, you just play it face down, and immediately gain money depending on the round the card is played. At the end of the game, all cards are checked one by one, and whoever scores most for each one takes the corresponding money prize.
If played early on, a bonus card can give you a good quantity of money, but then the other people may try to "read" your game, deduct which bonus card you may have played, and try to "steal" you the big prize at the end of the game.
Planner - also not sure about this one. Why rolling at all? It seems like it says: "you can freely choose your die actions without rolling". How does it work with order tokens?
The speed element is not gone, just the repeated rolling is. You roll dice once to have a random start, then you can choose what you want to keep (and place it on the Pig board), then change the rest while placing each die on the Pig board... but you still have to be quick, because it's still the first player who puts all of their dice on the Pig board who can take the 1st Player turn order token.