You might also want to look at ExpressionEngine. They have a free version that will allow you to install it, play around with the template system, and put up a basic site with some fairly good, solid features (easy to maintain, customizable templates, can export templates to DreamWeaver, easy-to-integrate site search).

Then, if you decide that you want to invest in the software, you buy the commercial package, follow their easy-to-understand instructions for upgrading to the paid version, and start playing with the new features.

If you're new to web hosting, one bit of advice: always make backups of your own. Always. Always. Always. You might not need to use them for five years...but if anything should happen, if you should find yourself with a host that has a bad server day/week/month, you're safe.

Like many of the folks in this thread, I would also advise: start with a small hosting plan, then increase as necessary. Upgrading is relatively simple, once you see the need. Paying for resources that you end up not using, though? Why do that?