Basic Roll/Guess game with 1-100 rolls

Hey guys, I'm taking a C++ class over the summer I'm running into some problems. I'm implementing a simple roll game. Here's what I've done so far:

1) Asks user to guess from 1-100 2) Let user know if his answer is above, below, or equal to the roll 3) Asks user if they would like to play again

However, I am supposed to "Compare the number of guesses necessary, on average, for 1-10, 1-100, 1-1000"
How would that be possible? would I not have to change the roll in the program so that it rolls from 1-1000 and 1-10? if I am having to change the code, how will I compare it?

Secondly, I am supposed to "Analyze the strategy of guessing from at least three different users and compare them in a few paragraphs. How does this strategy work within the algorithm you developed? What would you change within your algorithm or code to make the game easier or harder, based on this information?

I'm not sure where to begin with this one. Any help would be greatly appreciated!
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