To be clear, for most all people, it is safe to run Bleachbit non-sudo and check every box except
custom, memory, and free disk space (usage).
When running bleachbit as root, actually the same rules apply.
On Windows, using the memory checkbox is generally safer (rather, less likely to force you to reboot), but I’ve noticed on Debian and Arch-based distros (have not tried the other Linux flavors, I mean, why?) that the memory function will often have weird ill-fated results, such as
red failure errors (especially when ran as a regular user), Bleachbit, and other open programs, crashing or becoming unresponsive – as well as things like your clipboard, active OpenCL cache (3D renderings, hashcat potfiles), and some other significant, “force-you-to-reboot” probrems.
Also, you should be able to run all Adobe Suite software under Wine/Winetricks. I’ve gotten everything I’ve tried to run flawlessly (Photoshop & Illustrator CS6, as well as Creative Cloud as a whole).
e: Also, curious, what is your intended effect of running Bleachbit? Do you need to clear your disks of temporary space? I’d user Stacer for that. Do you need to clear illicit, illegal, or sensitive information from prying eyes and world governments, including bits floating around in your RAM ready to be frozen (literally) and ripped into a threat actors session-stealer? Are you needing to wipe SSDs so that they factually cannot be forensically data-recovered? Use dd and the trim() function for that.