re: Disney Pros, is it worth it to stay on site?

You can also Uber to the Contemporary and just walk across the parking lot to Magic Kingdom. Uber costs around $30 from the airport and yes they are allowed at MCO to pickup now. Last I heard, they were planning on having a Social Media pick up spot like MSY has. Not sure if they have yet though. We always go with a limo service with a grocery stop on the way in.

eta: This is from the Uber site about pickups at MCO:
"If you selected uberX or uberXL as your vehicle option, exit via Arrivals on Level 2 and wait for your driver curbside.

If you selected UberSELECT, head to Level 1 and walk to the Express Pickup Tunnel located directly next to the rental car counters."

Hope that helps.