I have 38 Word documents with at least 100 individual pages of information that I need to bring into Wordpress (either as pages or posts). I could copy-and-paste all of the content manually, but that would obviously take quite a bit of time. There's got to be a better way, but I'm not exactly sure what to look for.

I've heard that Word files can be exported as XML, and I understand that Wordpress can import XML...so would this be the way to go? Are there any tools that would help me with this task?

I'm a DIY kinda guy, and I've tried Google, but the problem is I don't know what the search terms would be in this case.

Any suggestions?

Personally? I would do them one at a time. One every few days.
Google loves new content.
Better to spread the content out, than throw it all in at one time, imo

I think I would do the copy and paste too. It would be tedious, but it really wouldn't take that long. But that doesn't really help you.

I would think if Word can export to XML and WordPress can import the XML it should pretty simple. At the very least you could export one Word document and do the import and see if it works to your satisfaction. You shouldn't need any other tools unless you're hoping to automate the export/import. A batch file should work for the export side of things.

If you search more I think something like "importing word documents to wordpress" would get you what you want if the info is out there.