I feel bad for a lot of those surviving Seattle bands who are still out there touring trying to make a living on a genre that thrived in the 90s but has lost a lot of stream since then.
The business has changed immensely in the past few decades - before the Millennium an artist could count on both royalties from album sales, money from touring and other miscellaneous income.
However, Napster and file sharing really impacted how we consume music and led to strong decline of music sales and subsequently means less income for the musician. If someone wants an artist's new album, they don't necessarily have to spend $20 on the CD anymore. If they want to hear that new song on a soundtrack, they don't have to buy it. They want that hard to find import CD with 1 new track on it, no need to buy that either. It can all be pirated.
Now don't get me wrong, I'm sure with the right management many notable artists from the last few decades have done well for themselves...but the key there is the right management. That means saving money and wise financial choices. Of course having good financial guidance could soften the blow of 90s (and prior) artists making less money from album sales and a decline in touring, either due to age or less of a demand.
I don't know if we'll ever truly know how his finances were, but even high earners can mismanage money and certainly that can lead to personal turmoil.