Hacker News Reader

At this point all packages work with Python 3. If you use ones that don't, they are not maintained, and you shouldn't use them.

[1] A one that I often seen was MySQL-python. That package hasn't been touched since 2014. Another one I've seen was PIL, that one was last released in 2009, and isn't even on PyPI, because it is that old, fortunately maybe because it's not on PyPI, people are more aware of Pillow which is a drop in replacement

Not wanting to update dependencies is fine, but in that case I'm not sure how it's an issue that you also have to use a certain version of the interpreter?

There is a pretty good chance they all have a python 3 version.

It's not easy to determine which versions of the library to upgrade to however. What's the latest version compatible with both python 2.7 and 3.7. Would be nice if pip had a setting to get that.

Sure, but even that is dwarfed by the equivalent problems in the ruby community. Most gems die after X years. Ironically some part of this must be explained by Python's enormous popularity.