Thankfully this town outside of Milwaukee has a large city to anchor it. In theory living in a place like Cudahy seems like it would be perfect for someone looking for a fresh start. Spending time on the Great Lakes is a plus too for those into fishing or just canoeing.
I find that the housing market is stable, with no major foreclosure issues and simple living is a must. If you allow the city to give it's best, then you will be very surprised when you are wowed by how quaint it is here. A great place to start would be South Whitnall Avenue, which is a major artery to get where you need to go.
The downtown area is also near Sheridan Park, where many people gather for 4th of July events and to catch the annual firework show. I know transportation is good here, I had to ride the bus for a few years. The stops are prompt and the rides are usually right on schedule.