When Holyfield was bad he was bad but when he was good he was bloody good. His pressure, incredible chin and inside fighting are what wins it for me against Wlad. I don't think he ever really fought anyone quite like Holyfield tbh and I think he'd find him self out of his comfort zone.
His willingness to take a shot and take two and his relentless body attack would wear wlad down and gets him a decision or a late ko.
They were two of the best and most dominant HWs ever and completely dominated some very good fighters. H2H both would be a challenge for any boxer. Also people underrate Wlad's competition he beat some very good fighters who would do well in any other era. Much better competition then other long reigning champs like Holmes or Louis imo especially if you compare who they all beat H2H
You mentioned wlad power, what I'm saying is you needed more than that to beat Holyfield. Wlad wouldn't have beaten the Tyson that Holyfield beat,his chin wouldn't have taken it.
Holyfield had more than just a solid Chin too. That's why he beat some of the best names in his era,a lot tougher era than wlad fought in.
He wasn't capable of winning 19 straight title fights and lost lineage to a guy who would've been a mid level Wlad opponent.