The bottom line for me is that I won't do the dining plan unless I calculate that it will save me money versus the next best alternative (e.g., OOP with TIW, etc.).
And I don't think having the plan is any more "convenient" than not having it. If anything, it's less convenient because of the restrictions involved.
Plus, if for example, someone in your party gets sick or otherwise loses their appetite, you throw away those unused credits (purchasing a dining plan is basically a gamble that no one in your party will get sick or otherwise lose their appetite).
Outside of potentially saving money, which is now only the case in increasingly limited circumstances (e.g., lots of character meals and other TS all you care to eat ADRs with kids under age 10), the only other real (albeit psycological) advantage to the dining plan is providing an "all-inclusive, paid up front feel."
But if a "paid up front feel" is that important to you and a dining plan will end up costing more than paying OOP, I'd suggest buying Disney gift cards and using these to pay for the meals (can even be used to pay for tips so you can concievably use these to pay more up front than with a dining plan).