Your driver idea cracks me up (although the Driver’s consistently been the biggest problem in my campaign largely because of how their vehicle stats work).

One of the things about Legwork is that you often also get other jobs and side-projects. Hitting the streets usually leaves folks with some side problems which spin out which then leads to the Legwork phase acting as Downtime. It’s also usually where I introduce personal stories and drama. In general it works ok – but I think your fears are probably legit.