&gt; Both sides are extremely persuasive and thus I felt that <i>no matter what choice I made it was the wrong one</i> and would haunt me down the line.<p>It really isn&#x27;t that big or hard of a decision. For the vast majority of projects, the choice doesn&#x27;t matter, so I&#x27;d default to Python 3 at this point. Really, the only reason to choose Python 2 for a new project is compatibility with libraries you need[0], but the list of Py3-incompatible libraries is constantly getting smaller and smaller.<p>That said, if you already have a lot of Python 2 code written, there probably isn&#x27;t any point to upgrading--the benefits are marginal at best, and it can be a lot of work to migrate a large code base.<p>[0]: Here&#x27;s a pretty good reference for Python 3 support in popular libraries: <a href="http:&#x2F;&#x2F;py3readiness.org&#x2F;" rel="nofollow">http:&#x2F;&#x2F;py3readiness.org&#x2F;</a>