Nope probably not unless it’s an even switch cost wise.

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Better in what respect? In some yes, in others no. Both sets should be about the same speed. Zipp 808 in front should be better to handle in the wind. HED should offer better braking. Zipp disc should be stiffer (and sound better when putting in big watts, but that's just me).

Overall, its probably a tie between the two, so I would stick with "never change a running system", and certainly not spend too much money on a potential switch

Definitely not. You could move to the newer Zipp and get better braking and marginal improvement if any improvement in aero. With HED you could move to the HED JET+ and get a wider rim and even better braking with their JET+ Black etched brake track.

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I think the old Zipp 808 was a little less sensitive to tire width than the old Hed 9 fronts. So if you insist on a front tire wider than 20C, go with the Zipp front. The Hed disk is superior to the Zipp disk with any tire (I did a fair amount of testing of this back in the day).

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I currently race a HED Jet 9/HED Jet disc and don't find it to be any different than my old 808 FC/950 disc setup. Except that 950 is awesome in regards to weight!

The deciding factor for me was that, in a garage full of wheels with aluminum brake tracks, I wanted my race wheels to be same.

I don't think this is a worthwhile upgrade that you're considering. Keep the Jets and keep rocking!

Thanks for all the responses. I have been very satisfied with my HED wheelset and have put some good times on them, 4:45 Ironman bike split. I will just stick with my wheels and keep pushing my upper limits.
Thanks again!