I'd like the ease of paying the tip by having it charged to my room, but we have had our meals charged to the room on three different dinners while on DDP.
This was
after telling the CM we were on DDP at the beginning of the meal.
Sure they can fix it, but it's just not worth the hassle. We decline the ability to charge to the room and it prevents this from happening.
Now with the less-attractive, less convenient dining plan, we'll have to go to an ATM before our trip to get a supply of tip money.
Same here! On two different trips we've had problems with the meal or part of the meal being charged back to the room. We use the DDE card for any extras (i.e. alcohol) along with the DDP. Whatever we use the DDE card, we charged using the room key. On two different trips we've had servers mess up and charge our entire meal to the room, instead of using the DDP. Now when we check in, we just allow charging privileges on one room key and then make sure we never use that key at a restaurant. However, I also travel solo to WDW a couple of times a year, so can't do that on those trips. On my solo trips I'll carry an envelope each day with enough cash in it to cover my tips and make sure the servers never get their hands on my room key.