Here is an excellent infographic comparing the features of wordpress.com and wordpress.org. I have often been tempted to go with a wordpress.com hosted blog because of the constant updates needed when you self-host. But there are just too many limitations for me.
How about you? When did you choose either to self-host your own blog or allow wordpress to host your blog for you on wordpress.com? One surprise I found is that wordpress.com actually puts advertising on your blog. You can get it off the blog and be advertising free by paying a fee. But for the fee you get charged to get rid of the advertising you could pay for professional hosting like you can get here.
Actually if you sign up for hosting with bluehost here I will set up your wordpress.org blog for free!
This infographic is brought to you by the folks here: http://websitesetup.org/create-blog/ They have a blog post showing you how to set up your own blog as well if you are so inclined.