Need Word Scramble advice

I am very new to C++ and programming in general, I am not looking for anyone to post actual code. I have worked through several books and tutorials. I want to create a word scramble that displays a scrambled word and as a hint the word definition. The program is also going to difficulty based (easy, normal, hard) with approx 500 words for each difficulty. I believe using header files would be the best way to go. 1 for each difficulty as well as 1 for the algorithm to select and scramble the words - so 5 header files. Is this assumption correct? I also am not sure the best method for implementing each list, but I am considering using enum.

I appreciate any offered advice or links that might assist in my endeavors.
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Have you considered storing the dictionaries in a file?
If I were doing this I would break the problem down to simplify it and then solve each part step by step.

For example:
1. first write a simple program that takes user input of a word & then it scrambles it and outputs the scrambled word. Once you get that to work, you know that you have working code that will scramble the word input.
2. Next I would write a program that can read a file containing words. The program then scrambles each word and outputs a file containing the scrambled words.

I would not worry about the difficulty level until i got the program working. It should be a lot easier then once you get the core of the program right

Once you get that done you could then write a program that goes through a file containing the scrambled words and gets user input to 'guess' what that scrambled word really is.

I think what you are asking is really about the data structure that your program should have rather than header files. You need to make it modular. The best design answer may come to you naturally if you devise your program in parts and then combine the parts to make what you want. I don't think you should try and write it outright without breaking the problem down as there will be a few sub problems that you will need to solve first.
Thank you for your responses. I will work on your suggestions and hopefully have a working prototype in a few days. Ultimately I want this program to help build my sons vocabulary in a fun and interactive manner.
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