While visiting family at the beach in New Jersey this summer, I was glad to see bicycle lanes had been painted and were being maintained. Then came the first bike — going the wrong way. Keep in mind, these routes consist of parallel, block-separated one-way roads (one each for north and south), so there's only one way for bikes to go on either road. This is a problem because, typically, drivers only look in one direction when turning onto said one-way roads. Often, they'll briefly check the other way for pedestrians, but bikes may come up fast.
Anecdotally, I've noticed an uptick in bikes in the area, and I've witnessed many drivers (including myself) get into close calls. While the other comments about urban planning and properly designing "bike friendly" streets are correct, bikers must share some responsibility and avoid making bad decisions.
Also, on the topic of pedestrians: there are unfortunately many people who hold a "car first" mentality, and simply won't stop for walkers. Fatalities among pedestrians and bicyclists in the US have a significant cultural component that mustn't be overlooked. Perhaps better pedestrian infrastructure would encourage better behavior.
I don't see this mentioned anywhere here, but there's a website I came across years ago that allows you to do the same, but you just scan the sheet instead of mailing.
Albeit it's not entirely free (pricewise or otherwise). I still think your second idea is better, where a learning algorithm "captures" handwriting and generates a font or more text with the same style. I can only imagine the implications in authenticity and forgery, though.