We rented a car in Orlando and parked it for a week at Port Canaveral. We needed it on either end of our trip for a couple of days, so it didn't make sense to rent and return. I watched the prices of the rentals daily and they can fluctuate a lot, so I got the best possible price and it was better than renting and returning.
I know you aren't in FL, but I'd still watch prices on rentals. As long as you don't put money down, you can make reservations and cancel them up until your trip, so you don't have to decide which method you prefer until much closer to your trip. Also, if you have a Costco membership, check out rentals via their travel site. They may have some deals, although not every day is a good deal day for them.
Regarding your hotel plans, for my family, if we arrived at 1:30am, we'd be sleeping in the next morning if we didn't have to be somewhere, not getting up for pool and brunch time. But everyone's different and you all may be too excited to sleep anyway.