Item 16 is one of those which is problematic.
The situations referenced cover many things over various periods of time, including some referring to any time ever. However, the eligibility period itself is NOT relevant to any of them (although one applicable period of time incidentally corresponds to the same period of time as the eligibility period -- referring to whether or not the applicant had been prohibited from being granted citizenship due to misrepresentation within the five years prior to applying, which of course is the same as the eligibility period, but this derives from a separate prohibition provision unrelated to the eligibility period).
Thus, the applicant needs to carefully review all the listed situations, including their respective references to applicable time periods (at least one refers to the previous ten years for example; many refer to the four years preceding the day the application is made, at least one refers to any time since the applicant became a PR), and discern if any apply. If yes, then check the appropriate box and add a supplemental page giving details about that situation. If, for example, one had been issued a Removal Order for a breach of the PR RO several years ago, but the IAD determined there were sufficient H&C reasons to allow the PR to keep status, check yes that one or more of the situations applies and add a supplement page giving details about that event. Despite the (erroneous) implication the form gives, that if any of the listed situations applies that means the applicant is not eligible, the favourably resolved Removal Order is among a number of scenarios in which the applicant should answer yes and give details without any worry that it will be a problem.