Starting with Leica? - literally

The Leica M8 is a good entry level Leica, and gives instant feedback compared to gettinga film camera. You can pick up a gently used M8 for ~$2K, add a Cosina/Voightlander lens for $300 or so. If you like it, the M Model 240 will be in good supply in a few months, and still be the same price. The M8 has leveled off in price, you can always resell it for close to what you paid. You can also use it for a back-up camera.

Using a Leica: make up your mind to do it, practice, read some references and try things out. You can of course do this with any camera, the Leica will require a little more practice to focus and frame the shots.