Yes, Oakland has fantastic weather and natural beauty. It's the people that make it horrible. Are there even worse cities? For sure. Bu far. You listed two of them.
I lived in Singapore for a number of years. I can't fathom people thinking it's a top 5 city to visit. Think it's a way better place to live than to visit because of low crime and clean, but pretty sterile and soulless and mostly a concrete jungle (and not in a good way, like Hong Kong or parts of Tokyo or a New York City). When I'd have friends come through the region, I'd tell them to plan 2-3 days tops in Singapore and use it as a jumping off point to way more interesting places to visit in Southeast Asia.
For habitation (only including "larger cities" which provide employment opportunites)
Denver MSA
San Antonio
Austin
Orange County CA
Bellevue, WA
I'm trying really hard to understand what "pre Obama" means. Help me out here?
Sure, that means before Obama implemented his plan to tear down the nation. Before these cities were overrun with homeless people, police defunding and woke insanity. Open your eyes and you can see.
1. Chicago, IL 2. Asheville, NC 3. Duluth, MN 4. Portland, Maine 5. Scranton, PA
Places you'd think are overrated/overhyped but actually aren't: 1. Aspen, Vail 2. Pretty much everywhere in Mexico and Spain 3. Charlotte 4. Las Vegas 5. London
Overrated:
1. Flagstaff 2. Cologne 3. Prague 4. Miami 5. San Francisco