I've never been to the Smith Playhouse. The walk is okay, but across a MAJOR intersection for you. I think you'd be better off with a $5 taxi. When you're done you can call 215-333-3333 and a taxi can come get you. It will also be about a $5 taxi from 30th Street to your hotel.

The Windsor is very walkable to the Academy and is also quite easily pricelined on using the info provided above.