The web is filled with such comparisons; so, I won’t talk much about the difference or the reasons to move… I’ll just simply say that you have to move to .org when .com is not enough. WordPress.com is usually enough for normal user. “NOT ENOUGH”, on the other side, is when you need more control, flexibility, or extra features…
Let me first mention that on WordPress.com, you’re using the Open Source WordPress System in the way Automattic Inc. chose for you. When we say WordPress.org (self-hosted), we mean that you’re using the Open Source WordPress System in your own way.
How to move?
When you decide to move, you need a hosting to install the WordPress System. Good companies provide it installed or ready to install. Then, you need to move your data (posts, comments, followers, …). The process isn’t that difficult but needs another post to explain it in details.
Hetzner is a good hosting company.
WordPress.com is offering this too through its Business Plan. In other words, upgrading to Business Plan is the easiest option. They’ll do everything for you. It might be expensive; but don’t expect you can have good website with good performance at much lower cost. This point is very arguable though.
Many hosting companies include it in the hosting price. Please refer to my post Let’s talk about domains
In general, the less you install the better your performance is. This is another arguable point. The dilemma is that, sooner or later, you’ll need to sacrifice at some point. That’s, if an installed plugin can do a job, it might not wise to install extra plugin to do similar job…
Basically, you need the following plugins: Cache (could be provided by the host), speed optimization, backup, and mailing/SMPT (the needs will be changed over time). More discussion about this and WordPress Performance Plugins is on: Why I host with WordPress
Jetpack Plugin: If you need a similar experience to what you have on WordPress.com (free, personal, or premium plans), then you have install Jetpack. You need it to stay connected with your friends from WordPress.com’s community. Jetpack is mostly free and the advanced features are somehow expensive. However, you might need to practice the sacrifice dilemma I mentioned above; I mean subscribing to Jetpack to avoid installing extra plugins.
I guess it’s clear now why I emphasized the word “enough” not “cost” as a criterion to decide when to move. When you move, moving back could be impossible. If moving is done in the right way, I believe you won’t look back.
If you need assistance in moving to WordPress.org, don’t hesitate contacting me.