In the example of the hail damage, due diligence was practiced. If the old question was asked less than a year ago, and it doesn’t answer your specific question, then ask it. To be on the safe side, it would be prudent to add in the details that you found “this” older and similar question (and share a link to it), but the responses didn’t provide the guidance being sought.
My guess is that deleting duplicate questions pertains more to current event topics that are almost identical and show up in a very short timeframe, e.g., a Jelly celebration, national or global news, same question repeatedly asked by the same user, be it sincere or spam. Then there is the occasional troll, like Pink Panty Guy, who pops in once and awhile to give us his latest version and a good laugh.
Anything beyond that should be allowed a free pass IMO. If a more experienced Jelly picks up on it, then they can flag it and/or hospitably share a link to the other question with the comment, “You might also find some help from the answers on this similar thread.” There is no reason to intimidate a new member over something so trivial.