I really like Steely Dan, but their latest studio album, from 2003, didn't even go Silver.
I'd say they face the same challenges as every other group of great musicians.
The market is flooded and a level of recognition is determined, to a large extent, by how much push advertising someone is willing to expend on your brand.
It's always good to hear about a true ground swell of some particular band that makes it through and breaks out on it's own merit, but it seems very rare these days.
It's a good time to play music because it makes you happy and makes you feel good.
best regards,
mike