There's Hyatt and Spring Hill Suites in South Side Works. and a Sheraton in Station Square. Is your goal to leave from the Point or just make the ride? If you're just riding staying in the Waterfront in Homestead might be cheaper. As for crossing bridges I wouldn't worry too much about it as there are plenty of options. You can always cross on the Ft Duquesne bridge from the north shore or the Ft Pitt bridge from downtown. I commute from East to West through Pittsburgh rush hour frequently and my only advice would be to stay off Carson St as it can be frightening... Also depending on when you come the switchback to the Smithfield St bridge might be done. It looks like they're readying to pour the concrete, though they don't have guide rails up yet.