You can lose wind-resistance by crouching forward slightly. Or you can avoid that route altogether because some routes are just too hard whichever bike you choose. ... One of the most overlooked virtues (and often avoided) of cycling is that you can get off and walk when it gets too hard or impossible.
Whatever the choice you make, you ought to visit your local cyclist shop and ask about gearing. You know like Gear-Inches, proper gearing tips and stuff. Most of em are nice, and sometimes they can give you the whole training for free. My LBS people have been great.