Let's make "mastering proper shoe care" an unofficial requirement (and rite of passage) in becoming a real adult, starting specifically with how to take care of your leather shoes. Below, the basics to keeping your nicest pairs in tip-top condition, rain or shine.
Before getting started, make sure you're in a well-ventilated area (translation: open a window!) and put down some newspaper to avoid any miscellaneous polish stains. Now, onto the good stuff: use saddle soap or a smooth leather shoe cleaner to remove dirt. Let the shoes dry for a few minutes, then shine with an old cotton T-shirt or a proper shoe-shine cloth.
This step is meant to help soften and moisturize the leather so that, later on, the leather is less prone to drying out and cracking. You’ll want to look for a natural conditioner, which is absorbed directly into the material of the shoe, as opposed to a synthetic conditioner, which sits on the surface.
Whether you live in a place prone to inclement winter weather or not, there's no real reason not to "weatherproof" your shoes. Look for protectant sprays (or beeswax-based products, if you don't like sprays) that aren't oil-based — that way, there's a lower chance of leather discoloration.
Try using a wax-based polish, instead of a cream-based one, and polish your shoes often. As a rule of thumb, there should always be a thin layer of polish on your leather shoe. Weekly applications are recommended.
When it comes to finding a cobbler, take as much care seeking a great one as you would a tailor. If there's something really wrong your shoe (like the heel's coming off), don't wait until the last possible moment to seek a solution. Go to the cobbler before there's permanent damage.