> What has been your experience [converting Python 2 to 3]?
Many months.
Step zero is education. Your team has been programming in Python 2. You need to make sure they know the differences in the environments, how to use create cross-compatible code, and how to use six. They also need to setup a second dev enthronement, and become comfortable switching between 2 and 3 regularly.
Step 1/2 is prioritizing. Determine how important is the move to Python 3, and what other features and dev work will you have to sacrifice to make it happen. While having a nice plan in place may provide some level of comfort to management, you can be sure it will thrown out, amended, extended, and/or ignored throughout the project. Upgrading Python dev environments brings no near or mid term value to the company. So expect developers to continue their current work-load while also attending to this tech debt.
Step one is getting the libraries into shape. This is easy if your project only relies on actively developed libraries with good teams behind them, but nearly impossible for abandoned libraries with no new commits in the last few years. Sure in retrospect, it was a bad idea to use these libraries, but at the time, they were incredibly powerful or popular. Generally, for abandoned libraries, it's easier to find a newer Python 3 library than work on fixing someone else's code. But this may mean rewriting large parts of an app, and may alter functionality, so constant communication with product mangers and a flexible approach is necessary.
Second step is working on your own code. One or two modules is no problem. But more than a dozen takes time. Scripts like 2to3 are not helpful, you need to use tools like six and modernize.
Third step is testing. If you have a good team, then you should already have good tests with known coverage. In that case, you should make sure your coverage matches, and take a very hard look at the code that is not covered. If your tests cover less than say 60% of code, you need to invest quite a bit of time of either testing directly, or building many more tests.
Step 4 is partial rollout. There will inevitably be issues you didn't think about or catch, so you need to plan the roll-out carefully and either split traffic or at the very least be able to quickly revert.
Step 5 is to watch carefully for customer complaints. Any complaint may or may not be related to the switch from 2 to 3, and you need someone on your team who stays on top of that, and can communicate the issue to the correct module owner.
Step 6 is deciding when to drop support for Python 2 altogether, as there will have to be a time where you have the two environments running side-by-side while you're testing. After all of this work, you'd think this part would be easy, but in every organization some folks will be wary about dropping support for something that already works.
Obviously, this isn't just a linear progression, you can do some of these in parallel, and will likely have to take a step back a few times. My back-of-the napkin, experience based, non-scientific estimate suggests that a 100k LOC project can be managed by two developers in two-three weeks, but a 1M LOC project (including libraries) is roughly 5-8X that much work.