Hmm, I have an X52 without issue. I did lots of multi assignments.
It’s a pro, but I wouldn’t expect that to matter.
Another neat trick is that you can assign the same button/axis to different commands.
It allowed me to assign my brake lever (VKB-Sim MCG Pro) to both brakes (R+L).
Something I couldn’t do in X-Plane, for example.
Thanks for the info @DizzyBasket7278 
I hope this thread is useful for those people assigning their controllers.
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Same here.
It does not work with Saitek X52 Pro. I defined button D on throttle stick as modifier and tried to define a combination of D and pov positions. It does not works. And any other two buttons combination does not works. Only combination of button with axis works.
Worked perfectly first time. Thanks for the tip and information on how to do it.
Thanks for pointing this out, a very cool feature indeed!
It works on my X52 Pro. No problems at all.
I use the thumb button on the throttle as the mode switch and have set nearly every button and toggle switch with 2 functions.
I don’t know why is doesn’t work in your case.