I'm not an expert coder by any stretch of the imagination, but the linter built into Pycharm does a decent job of identifying the most egregious typing errors,

I'm not an expert coder by any stretch of the imagination, but the linter built into Pycharm does a decent job of identifying the most egregious typing errors, IMHO. I think a lot of it really comes down to how much domain knowledge you have with respect to the problem you're trying to solve. I tend to have to process a lot of data from unknown sources, with unknown and inconsistent encoding. Most errors either show up immediately in Pycharm when I'm coding, within the first few moments of running the program, or two weeks later when it encounters a bizarre batch of records in the 15 millionth row of the database I'm processing or some strange network error that I neglected to foresee. I personally don't see how compile time typechecking would make any difference to that latter set of errors (which are solely due to my lack of foresight on all the weird ways people find to handle data), and the first two sets of errors are usually resolved in the testing phase of initial program debugging.