Wow Trix, thanks for all the effort you put here. I'm surely not worth it!
I edited your post to meet the forum size limit, but left the attribution line so others can link-back to your original post.
I'll just touch on some of your topics:
Yeah, I too was a cradle-Dem. Born into it, in a family and neighborhood that was part of the old Democratic Machine. At various times in my life I was active in street-level precinct work for the ward-office (a constant), assisted several unions, worked as part of an independent mercenary city-wide organization, worked directly for several candidates, and even organized and led a small neighborhood voting bloc to assure my family & my neighbors were taken care of properly by the ward office.
I did the above for personal interests, with some of my family & friends being on the City and County payrolls, and my family & neighbors needing city services that came through the ward office. My work with our neighborhood bloc was the most rewarding though, and of all the political work it is that which gives me the most pride. Most of the rest sucked for the most part, and was purely transactional on my part. I was not a 'true believer' or a 'man with a cause', but rather I worked to improve my lot and that of my family and neighbors. But I will admit I absolutely loved the buzz on election day, watching my neighbors coming in to vote as promised, and then watching the returns flow-in later that night in the ward hall or at candidate's parties. There's no buzz like it, and it made me a lifetime political junkie.
I never pursued a city or county job even with multiple offers on the table though, but instead opted for a university education and corporate life. I wanted to have the option to be independent of politics, and to have the freedom to geographically move about - which I eventually did. However I did get tired of corporate life too, later on. I then found the ultimate independence in working for myself and assisting my wife in her professional business venture.
Once I left the city and the politics, I left the Dems and never reconnected until just now. I no longer had any need for party affiliation outside the city, but still preferred Dem Presidential, Senate, and Congressional candidates, mostly due to policy. Unlike yourself, I like Obama - a lot! So much so I took my kid down to see him in Grant Park on his election night. But the Dem Party as a whole had left me, and had left me for a long time. I couldn't stand Hillary. And Trump disgusted me even more. It really was a hold-your-nose-and-vote election.
The whole big-city Dem experience led me to dislike the local politicians I came to be in the presence of over the years. In person they are cold & fake, and quite honesty they have a sort of scary cut-throat way about them. Lie to your face with a smile, and stab you in the back quietly. Scum. Pure scum. My work with the unions has led me to still be a staunch supporter of unions in private industry, but not in public service. In fact, I saw enough that I am dead-set against public service unions. The ones I saw were abusive, in my opinion.
Anyway, thanks for sharing your thoughts. And thanks even more, for allowing me to share mine and my perspective.