Is there a way to back everything up at the same time (posts, comments, all content, theme, settings, plugin settings, etc) and then just transfer everything to a new server without it being a huge pain? Thanks.
Yeap. You can do that easily. Just take 'Home Directory' backup from Backup option under your hosting account. DON.
I actually recommend doing a home directory backup and databases backup every night. I have been glad of it, needed the databases once, lifesaver.
Be sure to also set up your server to backup the site every day. The cpanel backup feature will just backup the database, so, be sure to keep all of the image files and everything else on DVD.
You can use the above mentioned wp plugin to take the backup. Orelse, log into your control panel and you will find a back function. Just generate the backup.
I would recommend you to do a home directory backup and check it with your hosting account. If you are starting a blog on wordpress, i think it is a very good idea b/c it is very friendly user. My own blog is a wordpress theme and very easy to deal with.
you can use wordpress db backup plugin to take backup of your database. it is enough if you are not using any additional files in your blog like images, etc. and you can also take backup of themes, plugins you use under wp content folder.
I use wp-db backup plugin to backup my database via scheduling, and backup manually database if i want to make a quick change. I have once already restore my entire blog, and it went well, thanks god. When i restore my blog, i needed wp-content folder, so this video tutorial how to backup and restore wordpress might help, backing up with wp db backup and wp-content folder (which contains your uploaded stuff and also, plugins.)
if you are transferring from a demo site to a real domain then you can just change 2 entrieds in the MYSQL options table, this requires the db to be on the same server but allows you to change the domain name. as previously suggested export everything and them import it again, this is very easy...