Honestly that sort of thing is really interesting to me. I think Khabib vs. Asker is unfortunate because LW-sized is just way too small even for a low-tier HW, with Khabib's strongest skill being grappling. But I think someone like Leon Edwards has a total field day against Asker and hangs with plenty of low- to mid-level HWs.

I think a good archetype for a skilled light fighter to do well against fringe HWs is striking-oriented, with emphasis on cardio and speed rather than attributes like power and strength that now no longer confer much advantage.

Also on a related but less extreme note, I think top-tier MWs beat mid-level HWs even giving up 50+ lbs. It'd be bad as a career path for someone like Whittaker to hang around in the top 10 at HW and never really have a shot at winning the belt and take lots of damage undersized -- compared to just fighting at MW and being champ (before taking lots of damage against Yoel, heh). But that doesn't mean he couldn't do it. I think people disagree with that, mentally simulating it based on how fights go when fighters are similarly sized (which, fair, HWs would nuke MWs a lot). But realistically, the top MW would put a much greater premium on evasion and attrition, and have the skill advantage to do that well, and the contests would be a lot more point-fighty.