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Upgrading is hard. It’s especially difficult for non-geek computer users who want every new-fangled feature without any learning curve or additional cost. ‘I want the best, the most modern and the highest-quality,’ they exclaim, but ‘I want it to work exactly like what I have now’.

My dad is one of these people. He’s a computer-literate, (i.e. he won’t delete files he doesn’t understand and follows instructions well, but usually needs a demo with any new software) 62-year-old salesman who knows that the latest software is likely to make his job easier.

But when he realized that InDesign 2.0 wouldn’t run on his new iMac with Lion and that an upgrade to such would cost many hundreds of dollars, he freaked. I’m fairly sure he yelled (via chat) at the Adobe representative, but who could blame him? He was used to a certain way of doing things and InDesign was set up with everything he needed.

Then I told him about Pages. He dismissed me. Then I told him again. He went back to looking for a cheaper Adobe Suite to buy. Then I made him an envelope in Pages, recorded me making it via Quicktime, and sent both the template and the short video to him.

He now uses Pages exclusively.

While the names are different, this same scenario plays out with businesses and parents everywhere, every day. They’re used to their free Blogspot, Tumblr, Posterous or WordPress.com blog, yet want the control that a self-hosted install provides. While setting such a thing up is trivial for power users, the maintenance is where most of us fall short.

Who’s going to update the plugins? Who’s going to make sure everything is backed up? Who’s going to be able to provide tutorials? I unfortunately do not have the time, nor is it usually worth the money, to look over client’s, parent’s or friend’s shoulders as they ask about every update and new plugin. And because teaching them the total ins and outs of WordPress doesn’t work because they’re not all that interested anyway, doing it ourselves becomes required.

And that’s why managed WordPress hosting exists, but that’s not always an easy sell, either. “$20/month for something I COULD do for free?” (I’m sure my) dad would say. But it’s not about the money, it’s about the peace of mind in KNOWING that this new piece of software will allow them to do everything that they need to do and most of what they want.

So how do you switch from a free service to managed WordPress hosting? How do you sell those comfortable with what they have on something that will work better?

You show them. Create a video. Make a slide deck. Narrate screenshots.

And get them on a managed platform. You’ll be glad you did.