This is where using frontier models can help - You can have them assist with configuring and operating wireguard nearly as easily as you can have them walk you through Tailscale, eliminating the need for a middleman.
The mid-level and free tiers aren't necessarily going to help, but the Pro/Max/Heavy tier can absolutely make setting up and using wireguard and having a reasonably secure environment practical and easy.
You can also have the high tier models help with things like operating a FreePBX server and VOIP, manage a private domain, and all sorts of things that require domain expertise to do well, but are often out of reach for people who haven't gotten the requisite hands on experience and training.
I'd say that going through the process of setting up your self hosting environment, then after the fact asking the language model "This is my environment: blah, a, b, c, x, y, z, blah, blah. What simple things can I do to make it more secure?"
And then repeating that exercise - create a chatgpt project, or codex repo, or claude or grok project, wherein you have the model do a thorough interrogation of you to lay out and document your environment. With that done, you condense it to a prompt, and operate within the context where your network is documented. Then you can easily iterate and improve.
Something like this isn't going to take more than a few 15 minute weekend sessions each month after initially setting it up, and it's going to be a lot more secure than the average, completely unattended, default settings consumer network.
You could try to yolo it with Operator or an elevated MCP interface with your system, but the point is, those high tier models are sufficiently good enough to make significant self hosting easily achievable.
The mid-level and free tiers aren't necessarily going to help, but the Pro/Max/Heavy tier can absolutely make setting up and using wireguard and having a reasonably secure environment practical and easy.
You can also have the high tier models help with things like operating a FreePBX server and VOIP, manage a private domain, and all sorts of things that require domain expertise to do well, but are often out of reach for people who haven't gotten the requisite hands on experience and training.
I'd say that going through the process of setting up your self hosting environment, then after the fact asking the language model "This is my environment: blah, a, b, c, x, y, z, blah, blah. What simple things can I do to make it more secure?"
And then repeating that exercise - create a chatgpt project, or codex repo, or claude or grok project, wherein you have the model do a thorough interrogation of you to lay out and document your environment. With that done, you condense it to a prompt, and operate within the context where your network is documented. Then you can easily iterate and improve.
Something like this isn't going to take more than a few 15 minute weekend sessions each month after initially setting it up, and it's going to be a lot more secure than the average, completely unattended, default settings consumer network.
You could try to yolo it with Operator or an elevated MCP interface with your system, but the point is, those high tier models are sufficiently good enough to make significant self hosting easily achievable.