This is too basic of a way to look at it. The past does count because it is why certain things have gravity in the present. The masses sure thinks so or the new era wouldn't consistently be compared to the past. The Network WWE has also says otherwise or they wouldn't have bothered to go to all the trouble preserving the past to help the sell current products. Not recognizing history will give viewers the idea that what they are seeing now is pointless. You know how they market "Where Were You When" for WM moments and so on?
Then again your post is playing devil's advocate I suppose.
No, I'm not playing devil's advocate. They're storytellers telling the story in a way that will benefit them most, by that I mean make them the most money in the here and now. They have to decide what details are important to that story and what to leave out, what to highlight and what to downplay.
I saw a serious question the other day from someone asking if Asuka's "winning streak" will be broken if she's eliminated in the Women's RR. Now anyone paying attention knows they call Asuka "undefeated," which they define as "never been pinned or submitted," she doesn't have a winning streak, she's lost before in matches that had multiple women involved, that's how WWE bigs her up, though, that's a story they're telling.
What value did Undertaker's "streak" at WM have? He's not undefeated, never has been, he's lost to plenty of the people he's beaten at Mania, but that was a thing they were able to hype up and sell.
What value does Roman maineventing three Manias in a row have? Nothing, there's plenty of PPV's and shows in between Manias that he hasn't mainevented. They put over Mania as a big deal because it's the largest PPV, so they create a value to having some sort of streak there and they're able to sell that as a big deal.
Is it a bigger deal to have multiple title reigns, or a few long title reigns? There is no set value to that, they'll hype up whichever one sounds the most impressive for the performer they're referring to. Roman and Seth both have title reigns that have lasted 5 minutes and 3 minutes respectively. That's not an impressive sounding thing, it's not a selling point, they sell the number of title reigns for them. They'll sell the length of Brock's reign with the UC and call him the longest reigning UC, they sell that Finn's the first one, never mind that he held it less than a day.
If the storytellers find more value in Cena surpassing Ric Flair, Flair had only 17 title reigns, they'll "count" whichever ones they need to, if there's more value in Ric being a 22 time champion, he'll retroactively be one and they'll find a way to tell the story that counts that, too.
Cathleen McCollough found a lot of value in highlighting Julius Caesar's relationship with Brutus' mother. Historically we know about it from one note that she wrote him, his relationships with his wives are much more well known, but those are given short shrift compared to what she could imagine about the first relationship because that's the one that would sell the most and make the most money.
WWE's the same, nothing's real, nothing matters until they say it matters, it's a historical fiction that's constantly being revised. DX's invasion of WCW was a great big deal, did you know that? I do now, I just watched a network special about it. I remember it being barely a blip at the time, I mostly watched WCW, though. If WCW was still telling the stories, it never would have happened at all, or it would be a joke right now, whichever one had the most value.