Why should I trust that this will last longer, given the same people are involved? The fact that you charge $5 / month? What do I get for $5 / month versus, say, my own VPS running whatever blog software I choose for the same money (or less)?
I have run many personal servers. They all come and go. They get hacked. I lose interest. The content goes away forever, except if I'm lucky enough for it to get picked up in http://archive.org. Posthaven is like that, but you don't have to hope. It will get archived.
Self-hosting is great and I don't think we'll ever replace it. But for the vast majority of personal content out there, you want a caretaker. I hope you'll think of us when you do.
Instead, though, you have to deal with moving all your content, repeatedly, as your chosen "forever" or "lifetime" company goes under, folds up, gets sold and shuttered, changes terms of use and claims rights to your content, or any of the other bad things we've all seen over the years.
Vigilance is going to be required whichever solution you choose, but having said that, a properly set up, locked down server based on a stable server-oriented OS distro, is going to require very little maintenance, if you subscribe to the old ways. Don't fix it if it isn't broken, and keep installed software to the absolute bare minimum required. Analyze upgrades to see if they're actually necessary (the answer is usually "no"). Pick your blog software carefully, from projects with proven track records for stability and security, and apply the same practices of keeping modules and add-ons down to the bare minimum, and you'll find there really is not much you have to keep up with.
