Welcome, from SE Wisconsin!

I like the look of classic bikes too, but the practicality of a modern city bike cannot be denied. For example, down there in the hot belt, electric assist may allow you to get to work dry. Integrated racks are nice, as well as LED lighting.

What's your living situation? Have you ever considered a folding bike, so that theft wouldn't be much of an issue? Also, for multi-modal transit. Bikepacking with folding bikes is popular in the UK, for example. One could take a long, one-way journey, then simply take a train back with the bike folded up and in a bag.