It may seem like Photoshop has a personal vendetta against you and doesn't want you to be able to utilize the undo like you want. Personally, I quite like having the power to be able to undo infinitely.
Although Photoshop doesn't allow you to undo as many times as you want, you can at least increase the amount of undos you are allotted. Here's how:
Step 1: In your main menu, go to Edit > Preferences > Performance.
Step 2: In the History & Cache section you will see a number. You can increase this number to 1,000 (max).
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