Except it’s not, he thinks he’s consistent. Far left and far right are a matter of perspective, and from where he sits, far left is trying to not deadname someone, starting a union, or progressive taxation. His far right is somewhere past suggesting gas chambers for social deviants.
You’re 25, unless your dream job is social media manager, you have 10+ years before anyone starts using your age against you. No matter which job you take, you can always pivot, just spend a few minutes crafting a narrative.
You can learn at any company. The financial company is going to give you a lot of space to learn process and compliance, and probably be infuriatingly slow, but you’ll probably come out with a different opinion about risk. The IoT start up is probably going to let you have more independence and playing with rando tech, and you will learn more about work life balance and your own working habits there.
If you’ve never worked remote, take the contract and see how much that flex is worth to you monetarily. You might be surprised. I would rather rub shit in my hair than wear a suit to an office everyday. But then again, maybe you love volley ball that much.
A lot of places self insure, but some already buy insurance as you describe. Qualified immunity is a pretty high bar to get over, but some people do get settlements. I’d argue insurance should have to be bought by the officer, or their union to have any effect on their behavior.