Here it is, the ultimate stroller plan!!!
First, get a Disney Visa. You don't have to use it; just get it and you get 2 free stroller rentals a day (plus a meet 'n greet with a free picture with a Disney character, but that's a different story).
Next, get a cheapie umbrella stroller. If you're flying, it works great to hang your various purses, diaper bags, carry-ons while your little one rides in style to the gate. Then you gate-check it, and it's ready to go when you get off.
Use your umbrella stroller to and from HoJo to DL. That stoplight down at Manchester looks SOOOOO far away at night! You'll be glad to have a stroller! As a PP said, if somebody would offer to push me around in a stroller, I'd take it in a second! DD was nearly 6 and she fit comfortably in the Disney rentals.
So, when you get to DL, rent your stroller. You can fold up your umbrella and leave it there at the rental place; they'll put it aside for you. The rental strollers are sturdy, comfortable joggers with canopies and storage bins; very steerable, and much better than a cheap umbrella! When you go back for your midday break (I HIGHLY recommend doing this-- again, the kids weren't the only ones who badly needed this in our family! We ALL napped!) take your nametag out of the rental and hang onto it, as well as your receipt. When you get back from your midday break, you can go to the person handing out the strollers (rather than standing in line) and show them the receipt, and get another stroller. Alternatively, you can grab an abandoned one from the raft of strollers next to the security tables on your way back in. Put your nametag in, and it's yours. Ditch your umbrella near the rental place again. Nobody's going to steal a cheapie umbrella.
Tie a bright bandana or scarf on the handle so you can recognize your stroller quickly outside a ride entrance. They can be hard to pick out, in a crowd of 50 or so! And the CMs have to move them around sometimes.
This is how we did it, and it worked great for several reasons. We didn't have to lug along our big, bulky stroller (which would have been nice to use, but a large pain to transport). We got our rentals free, but still had transportation to and from the hotel at night. I gleaned all the tips off the DISboards here, and I was very grateful for how it all worked out!