I've been trying and failing to put together some formulas to describe the situation, and use them to arrive at numbers. Having more or less given up on that idea, I'll just ramble about the subject instead..
My priorities for this bet are (in order):
- Take the low on both opponents: Any bet of 422.50 or less accomplishes this.
- Have the option to take the high on either opponent with a double/split. A bet of at least 290 is required.
- Beat either player with a blackjack, if possible: In this case it is possible with a bet of 385 or more.
So, I would bet 385. This leaves me with 422.50 - 385 less a chip (2.50) = 35 to play with for insurance without compromising my main bet and I'm acting last. In the event that the dealer shows an Ace:
- If either opponent declines insurance, then I can decline as well and advance with the low if the dealer has blackjack
- If Villain 2 takes insurance, then I can take insurance for 15 to 35 more than he does to beat him if the dealer has blackjack.
- If Villain 1 takes insurance, then I can take insurance for 27.50 to 35 more than he does to beat him if the dealer has blackjack.
- If both take insurance for an amount within 7.50 of one another, then both can be covered by one insurance bet of 27.50 more than [edit] the largest of their two insurance bets. [/edit]
When a villain declines insurance, that's just a special case of insuring for less, where the amount of the insurance is zero. So long as the villain's insurance is small enough, a door is left open for you to beat them by winning a larger insurance bet of your own.
As you consider varying your main bet from the minimum of 290 to the maximum of 422.50, each chip added to the main bet also adds an additional chip to the insurance bet which you could afford to make while still being able to double/split for the high after losing it.
The amount by which a DD win overshoots the required target (win > 575, to overtake villain 1) determines how much is available for insurance.
At the two extremes - a bet of 290 means you can't take any insurance, while a bet of 422.50 means you can take full insurance (210?), should you wish.
Losing the extra chip from the main bet is compensated for by the 2:1 payout of insurance, meaning that by betting more initially you are extending your reach forwards with regard to the total you can reach by winning the corresponding insurance bet.
Things change when you reach the point where adding a chip to your main bet does not allow you to add a whole chip to the insurance (i.e. when you can afford full insurance). At that point you cannot extend the reach of a winning insurance bet any further forward - an additional chip lost on the main bet is exactly balanced by an additional 1/2 chip paying 2:1 on the insurance.
Trailing Villain 1 by 75, we want 2B - I > 575, where B is our main bet and I is our ins bet. I maxes out at B/2, so that is 3B/2 > 575, B > 383.33. So once we pass this threshold, increasing the bet size has no insurance-related benefits.
But I guess the question is also focusing on the low side. With two villains, one of them might insure and the other not. So there might be scope to factor in their most likely max insurance amounts (<50 for Villain1 and <25for Villain2 ?) and bet just enough to be able to make an insurance bet big enough to leapfrog either of those in the event of a dealer BJ, while at the same time keeping the low against the other, non-insuring Villain, in the event that the dealer does not have it.
This is the point where the complexity really starts to defeat me...