Used to spend a lot of time out there on business back in the 90s. Hated it the first two trips out, but it gradually grew on me. Now I really miss it. The driving is the downside, especially for someone used to living in Chicago, but if you live near where you plan on working, it's not too bad. I never priced real estate, but I had a frat brother living in a rent control part of Santa Monica very near the beach.
In general, I like Santa Monica and the areas directly to the south and east. Never got to know the valley very well, but I had one crazy night where we drove from party to party up there and came back down to Hollywood through the hills.
There are really cool parts of Hollywood. Seriously. I don't know if anything is affordable.
Was briefly looking at colleges for my daughter and became intrigued by Claremont and the area surrounding Occidental. That's a bit east but probably cheaper.
As far as your work, LA is the vanity capital of the world. I think you'll do well just because you're a straight up good guy who knows his stuff. You'll definitely need a slick web site, but it sounds like you've got that on track.
Best of luck to you.
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