If you're using Disney to transport your bags, you'll have to wait for them until after official check-in time, no matter how close together or far apart the resorts are. So the distance doesn't matter.
If you're dead-set on using a dining plan, especially the "free" one, for *both* parts of your stay, the best thing to do is to buy the tickets you'll need for the trip with your *first* package, then just buy the minimum for your *second* package, and do NOT use that second set of tickets. Just keep them. Some day you'll want to do a hotel-only stay (no package, no dining, JUST hotel), and THEN you can use the tickets.
Otherwise, get the "free" dining (or just dining package) out of the way with the first hotel, and make the second hotel a room-only reservation. Make sure the first tickets are, or can be upgraded to, what you need for your whole trip (with 10 days being the max).