Making a living on the internet is not a low skill entry level position with a pension.
Your argument that bad choices being a personal thing could be extended to your proposition that life has been hard for “many” in the Boomer generation.
The Boomers as a whole make bad choices that may be in their immediate best interests, but have long term consequences they do not fully understand.
The Boomers’ choices have resulted in an unbalanced government. Instead of a right wing and a left wing party we have a right wing and centrist party (thanks to Clinton and perpetuated by Obama).
The Boomers refuse to acknowledge group responsibility or personal responsibility. They are a generation that has manufactured their own suffering and now try to pass the responsibility onto the generations that followed them.
The only thing anyone is asking for from the Boomers is to step aside and pass the torch to a new generation, which they failed to do with Gen X, and now the Millennial for their turn. Meanwhile Dianne Feinstein refuses to step aside for a new generation and dies in office.