- Understanding Open Source and Free Software Licensing[1]
- Open Source Licensing[2]
And then Producing OSS[3] also contains a (very) brief section on choosing a license. It's worth reading though, for other reasons.
[1]: https://people.debian.org/~dktrkranz/legal/Understanding%20O...
[2]: https://www.rosenlaw.com/oslbook.htm
[3]: https://producingoss.com/en/producingoss-letter.pdf