Longtime lurker, first time poster. 
I have a Feb trip planned for my 9yo and me. We may still cancel, depending on covid numbers, but I’m clinging to hope that we will go. I booked a new flight which has us leaving Orlando at 840 pm. My thought is to visit MK that day.
I’ve never visited a park on the day we leave. I’d love some advice about how to do that without it being a crazy stressful day. We’re staying at Pop Century.
TIA
Welcome to the forum! I often spend some time at the park on the day I fly home. MDE will pick you up at Pop at least 3 hours before your flight (they will actually say to be there 15 minutes before pick up time). I would expect to be back at Pop between 4:30-5. You will need to get your bags from bell services and have time to go to the bathroom (although there is a bathroom on the bus).
In pre-covid days I had an issue one day leaving MK. I started to the bus an hour before MDE. As I go to the stop one bus was driving away. I didn’t make the 2nd bus because of the line. By the time I arrived at the resort my son and I had to run to the bus stop. It was was too much stress. I would allow double or triple time to take away that stress . Also, know that Uber/Lyft is a reliable back up plan.
Thank you. I appreciate your expertise.
We have also done this, although staying at Bay Lake. We stuck with MK. I did make a slight mistake and suggested riding the railroad train for a complete circuit before leaving; it took longer than expected and I was panicking - albeit totally unnecessarily. We left MK 75 minutes before our bus even with just a 10 minute walk back to the resort.
I would also suggest you think about maybe doing a half day in a park and then having a mid afternoon “lunch” before the bus arrives, but at your resort (or AoA at a push). And have a few snacks with you in your carry-on bag in case you get to the airport and find things closed.
And welcome to the forum! 
We did this in December. Staying at Boardwalk, we did HS on our last day so we could just walk back to the resort to catch MDE.
Given you are staying at Pop, I would suggest making HS your last day if possible so you can just hop on the Skyliner back for the shortest trip. You could also do Epcot, but with them opening the latest, it limits your hours. But with Skyliner, middle of the day or so, line will be short and you don’t have to plan around sporadic bus times.
Theoretically your plan makes perfect sense.
But personally the Skyliner is the last mode of transport I would trust for getting back to my resort for DME. Any issues during transit and you’re stuck. I’d rather be able to call for an Uber if there was no bus or I was running behind. Even if you were waiting at CBR to transfer, you’d probably need to walk over to the main entrance to get a pick up,
Hmm. You’re right. Wind kicks up a notch, there is lightning in the area, or the ride operator sneezes funny, and it seems Skyliner stops operating.
Still, HS as a final day choice still works. Take Skyliner back if all is well, or else take the back up bus. But it does mean planning for the extra time regardless.
Thank you all for feedback. Because 9yo loves Star Wars, we want a full day there. I’m thinking we’ll do a second MK day on the last day and leave plenty of time to get back to Pop. Has anyone flown to Orlando recently? I feel safe once we reach Disney but I’m nervous about the travel to and from.
We made a last-day visit before flying back a year or so ago. I was nervous about getting a mid-day bus back to Pop in a reasonable time and MDE wanted to pick us up 3 1/2 hours before our flight. To extend our time, we used Uber which will allow you to add an extra stop in your trip. We left our bags at Pop’s bell services in the morning. When it was time to go, we walked to Contemporary where we caught our Uber. He took us first to Pop to collect our luggage, then on to the airport. Worked beautifully.
I always do a park day on my last day and do an evening flight like you. However, I like to maximize my park time so I do Uber instead of DME.
DME always worries me a little on the way to the airport.
We get picked up 4 hrs before, for international flights. But actually all airlines still say you should check in 3 hrs before an international flight, and with luggage to check that means DME is actually cutting it fine. I think usually we get to MCO just about on time, but not to the actual desk.
It’s never been a problem so far, and in theory at least Disney should step up if we ever did miss our flight. But I don’t want to test that theory out. 
First of all, your departure time (late evening) is perfect for a stress-free final day in the parks. You really shouldn’t have to cut much short.
Secondly, DME should be fine but you might feel less stressed if you go ahead and plan to use Uber.
You could easily do a 1/2 day at Mk. Pack night before. In morning have a day bag that has wash up items, and change of clothes/swim suits w several zip lock bags. We rd the park leaving our luggage at bell services. Day bag also leave checked at bell services seperatly. We go to park and would return @1. Have lunch and enjoy pool for an hour or 2. Then you are ready to go for 5. Pick up bags at bell services
We are also doing MK on our departure day (in March) with an 8 pm flight. We plan to take a Lyft to the airport, which takes some stress out of the MAgical Express timing.
Everyone gave great tips. My suggestion would be to think about the fact that you wont have a “home” to go back to before your later flight. For that reason we are not rope dropping and plan to sleep in a bit. Then will have a late lunch around three or four leave the park to go back and get our bags.
Hello there, @royjoyahoy!
We always leave on a late flight. I second @DizFinder’s recommendation to take private transpo to the airport. The bell desk can hold your luggage (at least they do at BWI and YC) and you just go back to pick it up and call a car.
We also travel light, so don’t usually have bags to check- that’s also a major de-stressor. Have your boarding passes ready to go. We use the airlines’ apps and ask for push notifications in case there is something going on with the flight. Also we make use of whatever TSA fast lanes we’re eligible for.
We pick a park we can walk to (for us it’s DHS or EPCOT) ride all morning and then have a late lunch there and walk back. Maybe hang around the pool or do something on the Boardwalk- anyway, something close to the luggage so nothing prevents us from leaving at the appointed time.
One piece of advice is don’t schedule anything big for that morning, like a character breakfast. It is easier to have a relaxed, perfect last morning without that fuss and the chance that something will go wrong with a big event you’ve been looking forward to. It is a perfect time to poke around and see the little things you may have missed, soak in the Disney aura, and start thinking about your next trip!
This is true for the OP as they’re at POP, but I just wanted to add that the Deluxes do offer a bit more for the departure day. For example, there are showers in Muscles & Bustles at BWI where you can change after a couple of hours at the pool and I believe all Club Levels (if they ever come back) give you privileges for the whole day. This actually figured strongly in our choosing to go with Deluxe +/- Club Level, we wanted to optimize late departure/early arrival days.