A Python 2.7 to 3.14 conversion. Existential angst.

A bit of very large technical debt has just reached its balloon payment.

An absolutely 100% mission-critical, it's-where-the-money-comes-in Django backend is still on Python 2.7, and that's become unacceptable. It falls to me to convert it to running on Python 3.14 (along with the various package upgrades required).

At last count, it's about 32,000 lines of code.

I know much of what I must do, but I am looking for any suggestions to help make the process somewhat less painful. Anyone been through this kind of conversion have any interesting tips? (I know it's going to be painful, but the less the better.)