Timing is a fools game for sure. Bubble could pop next month, next year, or even later.
If you're old, make sure you have a good percent in bonds. If you're young, make sure you have 6-12 months saved in case of layoffs and keep saving - market will look completely different in 20-30 years anyways so it's not worth worrying about.
Well, there are plenty of famous artists who only became famous after they died. Contemporary popularity doesn't guarantee historic/cultural impact.
I'm not aware of the specific requirements of this program, but Iteland also has a case for cultural preservation, particularly with works in the Irish language, which may not have the international appeal necessary to make a good profit but are important for intrinsic reasons to Ireland.
There's also the case to be made that in order to become a great artist, you must first be a bad artist - and there aren't that many jobs for internships/apprenticeships in the arts, especially as some of the more "basic" jobs (cheap graphic arts, copywriters, muzak, etc.) are snapped up by AI.
I think there is an interesting discussion to be had about what an artist must have in order to qualify for something like this. I would also be concerned with "antiestablishment" works possibly being excluded.