We did this 12/29/2014. I think I posted the details over at easywdw though....
It was tons of fun! (We had several trips before that, and had spent a few days at WDW before the "epic" day). That 1:50 flight is going to be a challenge though (ours was later, I think we left the last park at 2pm, taxied to PoR to pick up luggage, then to airport).
So....if it were me...
I'd leave luggage with bell services where I was staying the night before, and just swing by & pick it back up on the way to the airport.
I've also made a couple attempts at the parkeology "all the rides" challenge recently, so here's my 2 cents on park hopping...
1) Love minnie vans, but the price is going up significantly if it hasn't already (not a flat fee any more).
2) HS to AK, with all the construction, this is messy - a couple weeks ago uber/taxi/minnie van all picked up/dropped off in the same area - but it may be all back to "normal" by oct 17. Double check when you get there to see what the best option may be. The drop off for taxi/uber at AK is very convenient. The Minnie van is also, but is by the buses, not near the other drop off/pick up.
3) AK - anything except FoP is walk on at rope drop.
4) AK to Epcot, uber/taxi/minnie van all about the same time wise/drop off/pick up wise I think.
5) Probably faster to walk to contemporary.....uber/taxi from there...
6) Security at MCO without precheck can take a long time......
7) HAVE FUN!