I don't understand either. First, you don't HAVE to fit two summer trips in. You don't HAVE to fit one summer trip in. You can do as many (or as few) as you want.
Second, is DL "Disneyland" or "Delaware"?
Third, are you trying to do two trips in the same year to celebrate two birthdays?
Last but not least, any trip(s) you want to take CAN be done money wise. Whether YOU (general) can handle the money required no one on this board can say. We don't know your salary, we don't know your expenditures.
Now, if you want to ask how much such a trip will take, that's something you'll probably get a answer to. But people would need to know where you're starting from, do you have your own reliable transportation (to drive) or would you prefer flying?