I think the main thing is that all the things that Patrick is mentioning is overhead that Colin likely doesn't want.
He's running this as a lifestyle business and not a company that wants to make millions. I agree that certain changes can be made that allow better value for users (the auto-payment ability being very important) but all these things add overhead that Colin doesn't seem to want. Each change has a multiplier of time, and extra stress.
Heck, he doesn't want to waste his time on fixing his logo to be sharper.
I find Colin's approach refreshing. It's rare to see someone (especially one so gifted intellectually) be so in tune with what they want out of life. Having freedom to do what he wants, enough money to enjoy life and save for retirement and providing an important contribution to the world is what Tarsnap provides.
I'm sure Colin will make changes to make it more useful but I think it will be in the context of what's the best for the users and not what's the best for his pocket.