If you hit twice, White will often have trouble coming down from the Bar with both checkers and this could be your chance to begin your escape from the other side of the board or on a next roll maybe you will make another home board point with the stones you have on the 10, 8 and 7 points. However, if you do hit twice, the downside is that you are going to be very disappointed if White rolls the super joker of 5-5, which will allow him to re-enter with both checkers as well as hit you back twice! Then you might become the one stuck on the bar, and without an anchor to boot!
The better play is to hit just the one blot on your 5 point with 8/5* 7/5 and make the solid 4-prime. White will have some return shots but can only hit one of your checkers. If you are hit, you will still have an anchor upon which to land safely from the Bar as well as quite a few return shots of your own, on both sides of the board.
You will have around 80% chances of winning the game if you play 8/5* 7/5 as well as about 45% chances of winning it as a gammon compared to about 75% winning chances, and 39% gammon chances, if you make the double hit with 20/18*/15*.
It is interesting to note that if we take one checker off of the 20 point and place it together with the one on the 10 point (which eliminates the 5-5 joker roll) it now becomes correct to make the double hit with 20/18*/15*.
So when you have a decision to hit more than one checker, take some time to study the board and keep in mind all the hitting factors in
backgammon.