My main point is that the amount of effort you have to go through to achieve that is very high, and I wish it was considerable lower. There are technological changes that could help with this, and legal changes that could help with this.
I think a comfortable place would be if you visit the same online location using your main browser using one IP, and a private browsing instance of that same browser on another IP (through a VPN, proxy, or just new public lease), it would be nice if there was some expectation they didn't immediately have a high degree of certainty you were the same individual. For the general populace, this falls on its face.
Tor has quite a few mitigations to help here (e.g. simulated window/screen values), and Firefox has started to adopt some of them, but as mentioned here on HN frequently, Firefox sometimes has problems with CAPTCHAs and certain sites (I haven't had those problems, but I'm also not usually using it through a VPN), and I know Tor is sometimes blocked outright.
The point is that until most these protections (technological and hopefully some legal) are mainstream, completely protecting yourself is a double edged sword, since you also ostracize yourself from some sites and services. Tor is the equivalent of walking around in padded, baggy clothes and a ski-mask. Sometimes, like in the snow, it may seem fairly normal. Other times, like at the beach, it may preserve your privacy, but it's very uncomfortable and may cause people to avoid you, if not outright shun you and run you off. If everyone starts wearing masks and covering their hair, if you do the same you probably have a fairly high degree of anonymity and privacy through it.
In summary, I think Tor is a useful and necessary tool, but nowhere near sufficient for where I think we need to be generally.
That's true. However, it's mostly one-time effort. There are Linux and TrueOS workspace VMs, pfSense VMs as VPN gateways, and Whonix gateway and workspace VMs. All in VirtualBox.
There's ~no configuration required for the Whonix VMs. You just need to point the gateway VM to the pfSense VM that ends the desired nested VPN chain. And if there are multiple Whonix instances, rename the internal network that the gateway and workspace VMs share.
For the Linux and TrueOS workspace VMs, it's just like any OS install. You do have more machines to maintain, but mainly that's just keeping packages up to date. All of the devices are virtual, so you don't have driver issues.
Setting up the pfSense VMs is the hardest part. But once that's done, you can use them for years. pfSense is pretty good about preserving setup for OS upgrades. And there's a webGUI for changing VPN servers. But it's harder than using a custom VPN client.
So yeah, it's not so easy. However, someone could write an app that papered over most of the ugly parts. That even automated VM setup and management.