What's important is that you understand how you eat, what you eat, when you eat and where you want to eat. That should drive the decision.
We simply don't eat the way that the dining plan is structured even with the new changes, we rarely eat snacks, and we'd never use the refillable mug (we don't drink soft drinks and although we drink coffee, we only drink that at breakfast and prefer the press pot then). We typically eat TS for breakfast and dinner (usually Signature restaurants), no lunch. We typically order 1-2 alcoholic drinks for dinner (cocktail & wine), never eat dessert, usually have appetizers and sometimes I have 2-3 appetizers instead of entree. So we'd be paying for stuff we don't want/use, we'd still pay OOP for other things, and it doesn't conform to our eating style. We don't do character meals and the only buffet we ever do is Boma for breakfast. We rarely do QS or CS. I would never pick something off the menu to maximize what I've already paid - I eat what I like and what I feel like at the time.
I also don't personally see the convenience or peace of mind that others cite in prepaying for my food if it's going to ultimately cost me more especially if it isn't how I like to eat, I have to order expensive stuff I don't want to justify it and I have to pay for food I don't want. If the potential cost is close whether dining plan or OOP and the dining plan conforms to your eating style, it may make sense since you don't know exactly how it will turn out when you are actually dining - in a sense both are just estimates since you may end up paying more over and above the dining plan for OOP costs, may eat less on the dining plan so essentially leave money on the table, or may eat more than expected when OOP. But if the cost isn't going to be close and you think OOP is much less, then budget for it beforehand and make you sure you have that put aside to cover it when you return home. It just seems odd to me to guarantee paying more for something so that you won't worry that might pay more for that something when the differential is significant. Still - at the end of the day only you can answer the question about which route works best for you based on your style and selection of dining. I think that, as long as you actually look at it and do your own analysis, whatever you choose will work best for you; don't rely on what someone else says works.
