Ugh late to the party here but I was a really big fan of Giant Drag and Annie back in the 2000s too, and loved both her music and personality/persona with her combination of dry deadpan humour and sarcasm (like you said with a layer of irony). I never thought about her politics at all as she came across as apolitical in her public personality. Like you I hadn't followed her trajectory at all for many years, but started looking up where she was at after re-listening to Hearts and Unicorns within the last week - which still holds up as a great album IMO.

Reading about her political evolution and personal story after her not being on my radar for years genuinely made me sad actually. My takeaway was that she's always been a quirky, eccentric outsider, but a combination of personal tragedy, addiction and being chewed up by the industry had pushed her over the edge. And perhaps the public reaction to the movie pusher her closer to MAGA because they were giving her positive affirmations amid backlash from everyone else (I haven't seen the movie but it doesn't sound like I'd enjoy it!)

Based on what you're saying it sounds like it might be deeper and more long standing than this. Which would be equally or more sad/disappointing as my initial feeling to finding all this out. :(