Neither is super up to date, but these should cover the important stuff:

- 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

https://opensource.org/licenses/category is the list of all Open Source licenses vetted by the OSI (open source initiative).

Other licenses may be open source, but you'd probably have to get lawyers involved to make sure. So it's better to just pick a license which the OSI considers Open Source.

If you don't want to rely on just the OSI, you can also check what the Free Software Foundation, Debian and Red Hat think of the license you've picked.

Moreover, picking an existing popular open source license is important because a and b being opensource licenses does not mean that they are compatible, i.e. they could still have mutually-incompatible requirements that prevent anyone from releasing a combination of a-licensed and b-licensed code.

You could look at the OSI here for open source definitions. https://opensource.org/licenses/category

A number of Affero GPL type license have started to emerge and the community source. We started working on our own version here to allow us to still monetize or share restricted versions with fewer legal concerns: https://github.com/buildlyio/communitysource

For people in your position, I like Van Lindberg's book, Intellectual Property and Open Source: A Practical Guide to Protecting Code.

https://www.oreilly.com/library/view/intellectual-property-a...

It will help you understand the relevant parts of the law (copyright, patent, trademark) as well as helping to differentiate between various types of Open Source licenses.

Worth a read : http://netbsd.org/about/redistribution.html

Take a look at the popular licenses from the OSI: https://opensource.org/licenses