I remember HHH saying Flair was old and needed to retire in 1998
Yeah, it was before he got his true main event push. After the nepotism killed his image of the working man's heel substantially, he just tried to mirror two loved heels, Lemme of Motorhead and Ric Flair. Along with Kliq swagger jacking, it made it a lot cooler than The Ultimate Politican that was his true nature.
He used Shawn to get to Vince, and then Vince to Steph. Vince respected his scumbag ways to Chyna, and offered him his daughter and fired the nuisance

, who was so over and legit, she held the IC title and fought dudes. Then he just sabotaged anyone under Rock, Stone Cold, JBL, and Taker. He gave Vince Cena though

.
But, he's never liked Flair. I've seen Flair be apart of angles and promos that I know he was put into to job his image. He only got proper treatment when he was supposedly about to be retired. I highly doubt Haitch respects Naitch as a man, because Flair has a lot of demons because of his alcoholism, and Haitch doesn't drink. He's like that with DX and The Kliq as well. The only people he respects are Kevin Nash and Shawn Michaels, because Nash is intelligent as hell, likeable snobbish, and a politician (albeit more humble). Michaels for reasons I don't want to speculate, and he is legit revered by fans and everything Haitch wants to be, except White trash.