I personally will pay a subscription for literally every piece of software I use if it means the software makes me more productive. On an hourly basis my time is worth more than $100/hr. That means if a subscription tool is $10/month it only needs to save me 6 minutes of time, per month, to make it worth it.

Hah! I would never, but I guess that's why good options exist for the both of us. If someone pitched me a six-minute timesaver that costs as much as a cup of coffee, I'd gently remind them that I bought an espresso machine years ago.

My fear of paid software mostly stems from not actually owning what I pay for. I know people who are (horrifyingly) unable to use Git without a paid GUI that handles everything for them. If one day they update their computer and it's unsupported, or if the developer quits updating it, they've gotta learn a new UI. I'd rather just learn how to use the original tool quickly, and save myself a few hundred hours with 2 or 3 macros.

To each their own. I've paid for too much software that has gone to shit in the past, and I'm perfectly productive with free tools I can actually own.