If you have Regular inspiration, you get a "Roll Again" as an option in checks. I think Bardic Inspiration should get a button right above it where you can roll that. Maybe a button for the 1d4 from Guidance as well, now that I think about it.
Cutting words is a difficult thing, which will require some careful thought.
I agree for skill checks, pretty simple.
For combat inspiration it’s a bit more tricky because the attack roll and damage all resolve basically instantly. I guess you could have the game intelligently figure out when inspiration should be used on an attack roll based on the value rolled, and just use it. And then there should be some visual and auditory feedback so that you know your bardic inspiration was used.
Cutting words...best I can think is just have it be a toggle, and then once again have the game automatically do it when an enemy rolls something that is in the range of cutting words turning from success to failure.