Moving to Pittsburgh, Shadyside to UPMC Oakland, and Shadyside to Brentwood commute questions

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Hi, I’m completely new to pittsburgh, but I will be attending Pitt Med in the fall. I was wondering how doable are these two commutes.
The first one is from my apt in Elwood street and College St. (halfways between S. Negaley and Shady) to UPMC Oakland, about 2.5 miles. Are there any dangerous sections here? how long/difficult is the ride.

The second one is much longer, from my apt, or UPMC Oakland to 2620 BROWNSVILLE ROAD (south of Carrick, at the corner of Maytide), which is about 8.5 miles. How doable is this as it crosses the river and I have no idea what the terrain is. There is a training camp I want to visit 3-4 times a week, and I’m really not sure how long or dangerous this trip might be. Any help would be greatly appreciated.

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