Strava, Google bike directions, and Lanespotter exist. Strava gives calorie info. Healthy Ride site and app (also Tranist App) has bike share locations. Times to bike is an interesting idea as the feeling of biking to work at 9:15 is very different from say, 8:45. Traffic is much lighter a bit after 9am.
Unfortunately, Pittsburgh doesn't have a Wiggle like in San Francisco (https://en.wikipedia.org/wiki/The_Wiggle), but there are a handful of routes one can use to get between Downtown and Bloomfield including Liberty, Penn, and the Cemetery that connects Lawrenceville to Garfield via virtually car-free streets. The new Pittsburgh Bike Map (https://www.bikepgh.org/2018/05/30/celebrate-11-years-pittsburgh-bike-map-version-7-now-available/) features the best routes but the only way to avoid the hills is to put your bike on the front of a bus or buy an e-bike.
Also, we should be looking into Play Streets in Pittsburgh. https://centerforactivedesign.org/playstreets/ and https://www.nytimes.com/2013/04/28/automobiles/where-share-the-road-is-taken-literally.html