In 2000, a mere year after his death, the promotion was already changing gears and making itself far more wrestling-centric again. Far longer matches, the introduction and elevation of Angle, Benoit, Jericho, Guerrero, etc., and the 'technical' wrestling sequences they brought back, may have been the ideal environment for Owen to flourish. Different types of matches were being embraced, and the performers brought in had the skill and experience to pull them off. Beyond the work rate superheroes, you had plenty of guys like DDP come in over the next two or three years who’d love to have a great match if only their opponent would oblige them, and perhaps Owen would’ve.
That same era, by the way, was one that embraced a type of quirky humor personified by guys like Angle, Edge & Christian, and the latter in particular is a sort of spiritual successor to Owen Hart (pouty, loud delusional man child), so just like in the ring, many of the new performers would’ve better meshed with Owen character-wise. The crass, sexual nature of the show that Owen was so uncomfortable with was also largely cordoned off, in a way, from the rest of the show. The early and mid 00s type of characters and their skits probably would’ve fit him incredibly well, as opposed to having to cram Owen, the man and the character, in there with ‘Sexual Chocolate’, the porn star and the pimp. Hell, even the friction between Owen and Austin would’ve been less of an issue, as Austin was gone for a year! Perhaps by the time Austin returned the two could’ve reconciled, even if they never became best friends.
Not saying all that would’ve blasted him into the stratosphere, but in almost every way the WWF that emerged almost right after his death would’ve suited him infinitely better than just about any period he was ever involved. Size mattered far less, wrestling mattered far more, and the personalities might’ve jived with his perfectly. Owen was also only 34 years old when he passed, and given the successes Jericho and Dustin Rhodes are enjoying today at 48 and 50, respectively, age would not have been a factor. Even if he stuck to his goal to retire young and leave ‘the business’ entirely, perhaps he’d have two or three excellent years as a cap to his career (I doubt that the retirement would’ve occurred as planned though, because wrestling).
Sorry for the novel!