I also don't want to be the bad guys here but:
"I'm paying $200/month for Claude Max on my own dime, not my company's. I'm a Technology Director at a Fortune 50 company, using Claude personally to learn and then advocate for the right tools in our enterprise environment. That context matters for what follows."
No it does not. It makes no difference if you pay or your company pays or if your product is making money or you are self-educating. If you feel that you are not getting a $200/month return on your investment then you should cancel your subscription. I also struggle to understand why you are using a $200/month plan to do investigation and testing when there are $25/month options.