Why even place them in other towns? Sims take ages to get from A to B using subways. Just taking a bicycle is so much faster, plus, subways look out of place outside of Bridgeport. But I heavily dislike them even there. Getting a Sim their own vehicle is preferable.
Fortunately, Polly didn't have far to the bookshop where she worked, until she quit. The subway is conveniently right outside her door. Having mastered the guitar, she can easily earn 5000 Simoleons in half a day's time or so.