When we bring a stroller (a single one in this case) we keep it with us and check it at the gate. I don't have any experience checking a stroller as luggage and having DME deliver it.
Keep in mind that your luggage will not arrive at your resort at the same time you will, so if you need your stroller when you arrive so you can go to a park (and in my opinion, you will), you may just want to gate-check it.
We are going this summer and while we have essentially stopped using a stroller with my 5 year old around home, we are definitely taking the stroller with us to WDW.