Have you tried the "My Location" choice when you're in Estero? Tap the widget so it brings you app up and tap the + button at the bottom right. Then tap "My Location." This will bring up a map with a stick pin that you can drag to the location you want. Then click done. If it says "Unable to retrieve location name," you can edit the name by clicking in the box that says "Current location" and it will add it to your personal list (not the big list of cities that comes with the app though).
When you are at the location, it should grab the city you set up on your list and display that. If you don't have GPS on, it may go by the signal from a tower nearby but not in your location and give you a different city name though.
If you live near a city with the same name as another in the list though, that's a whole nother PITA. I get the time for Riverside, CA whenever I drive through Riverside, IL. That got annoying enough for my to take the clock off the weather widget and use a different clock app. The weather would always work fine though.