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OP, what are you doing during the day before 2:30 when your DH is done with his conference? Could you Uber the bags over to POFQ during the day so that part is out of the way? Or even drive DH to his conference and pick him up so you can do the bag Then have your DH either meet you at DHS or pick you up from POFQ. Or another option is to have the Dolphin transfer the bags to POFQ so you don't have to stop there at all.

Another option would be to drop off and pick up DH from his conference so you have the car during the day and can drop off the bags at POFQ and then go straight to DHS after you pick him up. But this would assume you could add yourself as a driver on the reservation, which I know may not be feasible for a work trip.
OP isn't allowed to drive the rental as per her DH's corporate policy for rental cars.

I like the idea of Ubering to POFQ to drop the bags.
 
Not to be snarky, but I'm not sure you can get everything just trying way you want it without giving something up whether it is sleeping in or $ or walking to HS

Does your husband really care if he rides the rides you want to ride at HS? I would give up the sleeping in and head to POFQ in the morning with the luggage. Then I would enjoy HS by myself until your husband is ready. He can pick you up at HS when he is ready or you can take the boat and meet him to return the car and have an early dinner leaving you plenty of time to get back to HS for fireworks. If you're wwillingto spring for an UBER to the park in the morning (or maybe your first hotel has a shuttle?), he can load of the car in the morning before the conference while you sleep and you two could take care of he luggage/check in together around 2/3 before an early dinner. But then you have to deal with Disney transportation back to Dolphin for dinner.
 
Not to be snarky, but I'm not sure you can get everything just trying way you want it without giving something up whether it is sleeping in or $ or walking to HS

Does your husband really care if he rides the rides you want to ride at HS? I would give up the sleeping in and head to POFQ in the morning with the luggage. Then I would enjoy HS by myself until your husband is ready. He can pick you up at HS when he is ready or you can take the boat and meet him to return the car and have an early dinner leaving you plenty of time to get back to HS for fireworks. If you're wwillingto spring for an UBER to the park in the morning (or maybe your first hotel has a shuttle?), he can load of the car in the morning before the conference while you sleep and you two could take care of he luggage/check in together around 2/3 before an early dinner. But then you have to deal with Disney transportation back to Dolphin for dinner.

No snark assumed. I’ve come to the same realization- there’s no having everything here (and that’s okay and why I posted the question).

We didn’t plan on many rides (there are only a total of 6 that aren’t shows anyhow) so the ones I’m planning on, he also wants to go on. There’s also not much at HS I care to see that he doesn’t (in fact it would be better if I could go to the conference and he could wander the park but I think they’d notice).

I’m going to have to get up and drop off our luggage at POFQ (have him drop me off there with the bags and go to his last session). We don’t have much other choice.

Have dh pick you up after his conf. Go directly to PO from there. It should be quick...about 15 mins. Drop off bags, continue on to the Dolphin (about a 10 min ride), drop off the car. Take the boat to DHS. Enjoy your day.
When it’s time to leave, either boat or walk to the Dolphin for Shula. The boat takes about 15 mins once you get on and it leaves. Could be a longish wait for it to come and you get on. The walk is about 20 mins.
The question then is how do you get back to PO? I would just take Uber or a cab. Won’t cost much.

This is pretty much our plan now except he’s going to drop me off at POFQ, and meet me at HS after dropping off the car at the Dolphin. We’ll have dinner late (after fireworks) and then start our MK day later on Saturday if we need to sleep in. It’s either lose some morning time at MK or lose hours of time at HS when we’re already only spending half a day there.

We take the boat all of the time (we usually stay at BCV) and usually we don’t wait more than 15 minutes for it to show up (but everyone’s luck runs out sometimes so
I plan for the worst). We would have to Uber back to POFQ after a dinner that late (unless we take a bus to Disney springs and so on but let’s just not add another layer at this point).


Are you positive about that? Enough that you would chance returning a car after 4pm, knowing that if you're wrong, you're going to get hit with an extra day rental charge (that I'm guessing the company won't pick up)?
National’s policy is that cars returned after the desk is closed are considered returned the next day so we’d be stuck with paying for a day’s rental we don’t need. That changed things for us.

To those who had plans involving me driving, I can not drive the car. In order to be added I have to appear with my ID and then DH’s company will not pay for the rental. That’s his company’s policy and since they are gracious enough to not care if I stay In his hThursday night on their dime, I’m not pushing my luck.

Thanks all for the input. It helped me make a better plan. It may not be everything I wanted (sleep in on Friday, no extra transportation expenses, maximize time at HS and have an earlier dinner at Shula’s- and I am usually the one telling people they can’t have it all). I think I got really swept up in the idea of not having a 2 yo alarm clock and lost my mind for a minute.
 

I’m going to have to get up and drop off our luggage at POFQ (have him drop me off there with the bags and go to his last session). We don’t have much other choice.

I know you said you don't want added transportation expenses, but an Uber from the Dolphin to POFQ is $6.60. I would gladly pay that if it meant I got to sleep in like I wanted to. Then you could easily bus to DHS or have DH pick you up from POFQ on his way back.
 

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