Its certainly easier to stay at one resort, however when we did it it wasn't as bad as I thought, the worse thing is repacking your stuff. If your traveling during a slow season your 2nd resort may be ready in the morning or earlier than 4 PM, call the 2nd resort front desk when you check out of your 1st resort.
Depending on the # of days you will have at Disney, we found it easy to use the check-out/check-in day as a down day. We got up late, kids hit the pool on last time, we took our time checking out, left the bags with the bell hop, ate a leisurely lunch, traveled to the new resort, checked in early if possible, if not we hung out at the pool of the 2nd resort (just rememeber to keep your suits out). You can also do other things that require only a couple of hours at a mcuh slower pace than the parks and do require the purchase of a ticket. Example, mini golf, downtown disney, the boardwalk, or whatever you feel like depending on the time. This also allows some time to unpack at your own pace, versus trying to check-in and unpack after spending a long day in the park, especially if you go when its HOT.