If you don't put the yellow luggage tags on your baggage you will claim it at the Orlando airport and bring it with you on DME.
Our rule of thumb is that if we land at 5pm or later, we definitely bring our luggage with us ourselves and sometimes even if we land after 4pm we take our luggage with us.
DME says that they
should get your luggage to your room 3 hours after you arrive at Pop but there is also no guarantee. I estimate 2 hours from landing until we get to Pop. (It often doesn't take that long but it has taken 2 hours more than once.) Add 3 hours to that for luggage delivery. Personally, I don't want our luggage arriving at 10pm (or later). By that time on a travel day I want to be heading to bed, not starting to unpack suitcases.
As with many things, this is personal choice though. Other families may not pack 2 huge suitcases for 2 people.