There are potentially other patterns to meet 1000, these are just the ones I quickly succeeded with.
Guide to Hill's Pain and Pleasure
By far the easiest.
Choose options: "I... I'll have a try... I have heard of such stuff before." and "I'll be more rough!"
And you literally just SM anything for both sections.
You will get the "Cursed" ending.
The actions for Hill are exactly the same for Madoka's.
Choose Option: "No, that's not the way I love you!"
Caress her foot and thigh.
Choose Option: "I would absolutely satisfy you!"
Either lick her boob once then her meow, or just her meow.
You will get the happy ending.