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Is there a way to make it so that when I wake my computer from suspension (or hibernation), I can choose which OS to awaken? If so would this be operating system specific, or an option in grub, or something else?

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TL;DR: You can when hibernated, you can't when suspended.

When you are suspended, the memory of the current OS is still stored in RAM. You can't just wake up into another operating system from being suspended, because only one operating system can occupy the process and ram at a time. Having two operating systems with the same RAM won't work.

When hibernating, it's a bit different. Ubuntu will store the memory into the "swap" space you have set up, and completely shut down the computer. This means that when you restart your computer, you can choose to boot into Windows instead of Ubuntu.

Note that if you have two Linux distributions using the same swap partition, you won't be able to hibernate in one and boot into the other - they will both try to use the swap partition, resulting in the same problem when suspending. The reason windows can start when Ubuntu is hibernating is because Windows has a separate hibernation file on it's own partition.

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