Also, why don't you spend a couple of hours at Magic Kingdom before going to Hoop De Doo. (Unless that is a non-park day for you). That way, it won't seem like your using up a lot of transportation time.
If you are at the 5:30 Hoop, then head to MK about 2pmish, stroll around, do an attraction or two, then head to the Fort on the boat.
We always do a lot of park hopping and resort hopping, but rarely go to a destination where it takes two buses, or boat/bus, etc.
For example if we're having dinner at Beach Club, we'll spend some time at Studios or Epcot for a bit, then walk over to Beach Club, then have dinner, then after dinner if the parks are closed, then we bus to Downtown Disney, stroll through there a bit, then bus back to our resort. (We have no young kids though, so we generally are night people).