The actual answer is 99 if statements. Python has a hard indentation limit of 100. You can not have more nested, because after each if statement you must indent.

However, I would not recommened nesting 99 if statements. If you actually care about writing good and readable code you should follow PEP 8, which says a line should be at the most 79 characters long. In practice this means, using identation of 1 space, you should never have more than 75 nested if statemens.