A few thoughts on hosting your own blog
Installation Depending on your experience, this can either be an intimidating step or old hat. Word Press? has an extremely simple installation procedure, even for non-technical users, while Movable Type is a bit trickier. Both have excellent support - WP is free in the form of forums, and MT support comes with a paid subscription.
Upgrades It is vital that you keep your weblog software up to date. Security vulnerabilities can spread like wildfire, and trust me, someone is trying out known hacks on your site right now. Some blog upgrades are purely cosmetic, but almost all contain patches to keep your machine safe.
Most upgrades are smooth and easy, especially on basic installations, but see the section on Hacks below.
Backups I also cannot over-emphasize the importance of backing up your database and files often, and especially before any upgrade. Walker servers are backed up nightly, but I have a separate script to dump the databases to a local file. It's too easy with multiple authors for something to go wrong (at least once) and create an immediate need forpost recovery. Find a backupt system and method that you can stick to and then stick to it.
Hacks Sometimes there's no other way to get a piece of software to do what you want: you've got to go under the hood and mess with the core files.
Walker blogs use a (slightly) modified version of Word Press? so we can run all of our blogs with just one software base. This allows us to fairly easily upgrade all the blogs at once, instead of one at a time. (I'm told this feature is coming in WP, we'll see)
Be careful hacking your installed blog: too many changes will make upgrades difficult or impossible. Try to make your changes via plugins, or at least document your hacks so you can make a clean upgrade and then re-apply them.
It should be noted that WP has the ability to consolidate almost all necessary "hacks" into a template, outside of the core files - so upgrade will still work. This is obviously a huge benefit.