I would allow an absolute minimum of 90 minutes from flight arrival time to hotel check in...assuming the flight arrives exactly on time you have to get off the plane, hike the concourse to the tram stop, tram it to the terminal, hike to the DME check in, get through that line, move to the bus stop, wait for your bus, load and wait for others to do the same, then figure a 30 minute drive to the WL from MCO and then the wait to check in.
I think if you get to your room by 3PM it will all have gone off like clockwork... I think it would be at least that long or longer if you had to wait for your luggage and then waited again for a rental car...just takes a while to get from plane to room!!
There is always the possibility you will time everything perfectly, have no line waits at DME check in, bus stop or hotel check in and the driver "hits all the lights green" and drops you off first and no one in your party needs to make a potty stop....in which case you might get there sooner (but I am NEVER that lucky!!)
you should be fine for your Hoop ressies assuming the flight is not delayed....I would leave my room no later than 4:15PM for Hoop at 5PM.