I like the sound of your plan - I think that's a good path forward. I think most of us who live car free (though I cheat now - I married into occasional car use) find that we want more than one bike. I LOVE 28c tires as a do anything size (especially GP 4 seasons). So much is preference, but I think you'd find that most people going over about 15 miles prefer drop bars for the hand positions. I will say that my commuter rack is all over the place - MTBs, cross, old, new, roadie. Just get what makes you comfortable and happy - there's no one size fits all.