Fair enough, I do bash shared hosting, but only because, in the course of my work, I come across so many companies who either don't know how to make the jump to more reliable hosting or simply don't know that they should, that it would fix a lot of problems, ranging from uptime to speed to security.

In the case of this post, which you titled so provocatively, I felt it was directly relevant to point out the intrinsically scum-baggish nature of the shared hosting industry because they are the ones throwing mud here, not Matt. Unfortunately, because so many sites derive income from shared hosting affiliate links, the pitfalls of shared hosting don't get much attention but, again, it is directly relevant to the subject of your post.

That underpaid clueless kid would most likely be me and I wouldn’t know half of what that kid would know.

Believe it or not, keeping a server secure isn't so much about what you know, it is about whether or not you care and, let's face it, no-one is ever going to care as much about your site as you yourself. These days, keeping a server secure is just so much easier, so much less arcane than even a couple of years ago - the improvements in WHM/CPanel and the quality of tutorials online puts running a server at much the same level as being proficient with WordPress i.e. understanding how to fix basic problems and knowing where to look for answers when you don't have them yourself.

Despite the "Joe Everyman" persona you adopt to help make WordPress more accessible to your readers and listeners, it is clear that you are one smart cookie, running a server would be a snap for you, not at all the time-consuming nightmare you imagine.

In fact, I've often wondered if, at some point, you were going to parlay the reputation you've built up into some sort of WordPress-related business. I remember, a while ago, you expressed your frustration of having to juggle your website and podcast commitments with your real-world job, you even flirted with the idea of charging for access to your forum. Your current fascination with the premium end of things suggests that you are at least thinking about getting your hands dirty with PHP, getting some sort of product out there.

Have you considered, though, that offering WordPress hosting would be a much quicker route? I mean, you would have to sit down and learn a few things but, I know from listening to you discuss WordPress, you've got a sharp grasp of detail, you could get up to speed with WHM/CPanel in just a few days and, with a good server company behind you to handle anything non-WHM, you would be all set.

Seriously, when it comes to WordPress, you already know more than the vast majority of hosting companies out there. For instance, there is one company that I'm sure we've all noticed, they market themselves as specifically WordPress hosting, but they actually know incredibly little, all their installations of WordPress are just regular, non-modified Fantastico installs, with all the baggage and security problems that entails.

You, on the other hand, know pretty much all there is to know about WordPress - you might not know how to write a plugin, but you know all the ins-and-outs that it is important to know, you are already wired into the ongoing evolution, the ups and downs of WordPress, it's something that you obviously have a great interest in - the vast majority of human beings do not. If I didn't already know how to manage my WordPress installations, you are precisely the sort of person I would want to pay to do it for me. What you already know is more valuable than you think.

I hope you don't find it presumptuous of me to suggest that, I just think it would be a good match for your existing interests, you've already got a great platform from which to promote such a service and it would be in the interests of the WordPress community as a whole to see you establish a way to get well paid for the valuable role you play as communicator.