Is it possible to use Bento for Mac as the database for a database-backed website?

I'm looking to create a website on my Mac, with content coming from a database also on the Mac. The website is static, and I'll probably need to write some scripts that will periodically (1) create new HTML pages on my Mac based on new content in the database, (2) sync the HTML pages on my Mac to the web server on the Internet using SFTP.

Can this be done using Bento, or should I be looking into Filemaker Pro instead?

As far as I know, there would be no way for scripts to directly access the data in a Bento database, so you would need to manually export that data every time you need to update the website. If you don't have too many sets of data, or if the site doesn't need to be updated too frequently, this might work well for you.

Also, Bento is fairly limited when it comes to building relational databases. It can handle flat databases and very simple relationships, but lacks the ability to set up complex relationships between tables. If you don't need complex relationships, and manually exporting your data is acceptable, then Bento would be a viable option that's relatively inexpensive and fairly easy to learn and use.

On the other hand, FileMaker Pro is very scriptable, allowing for almost complete control through both its own internal scripting language as well as through AppleScript. It also handles much more complex relationships. Of course, this advanced feature set also comes with a higher learning curve (and price tag). However, FileMaker does have a large and active community of users that are very helpful, and there are plenty of tutorials and sample databases to help get you up to speed.

While FileMaker does have built-in web publishing, there is a limit of 5 concurrent users unless you get FileMaker Server, or host your database on a 3rd party FileMaker hosting service.

Bento isn't well-suited for your needs, in my opinion. It's possible to export information from Bento into a variety of formats, including text files, Numbers, or Excel. But it doesn't have the hooks needed to be queried by a Website creation tool. As you mention, FileMaker Pro does have that ability. Here is their web publishing page.

This may be overkill for you, but if you're familiar with SQL databases, you might also take a look at Sequel Pro.