The problem is that the right part of the flip-flop is never true, as it contains the $i < 2 condition together with the regex. If you want to stay with the flip-flop, I'd modify it to something like the following:

my $i = 1;
while (<DATA>) {
    if ($i and /Startpoint/ ... /slack/ && $i--) {
        print $_;
    }
}
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