Even I would have a hard time recommending that someone take transit from Reston to the Cathedral on a weekend. That's not the sort of trip that Metro serves well. Transit will not work for every origin-destination pair. Both system expansion and transit-oriented development will bring more such Os & Ds within reach of the system, so that it can capture a greater share of all trips.
Deferred maintenance will always be a problem as long as politicians get votes for ribbon-cutting new things but not for scrubbing old things. The escalators probably would have needed replacement this many decades in anyways.
Historically, Chicago was a collection of factory-town neighborhoods knit together by streetcars (now buses); the "L" and the Loop, even though they're how outsiders see Chicago, weren't part of everyday life for most locals. The "L" only carries a third of regional transit passengers; almost half ride CTA buses, and the rest are on Metra trains and Pace suburban buses.
Contrast that to Metrorail, which carries over half of regional transit riders; buses carry 45% and commuter rail a scant 2%.