Nix, may I please ask how you would distinguish between the Machairodonts and the not-actually-cat sabertooths (like the Nimravids or the Barbourofelids) in you were ever inspired to draw them side by side? (also, may I please ask if you have ever illustrated one of the Amphicyonidae?).
I’d distinguish the “false sabertooth” nimravids and barbourofelids by making them visually less cat-like, since they’re non-felid feliforms.
Differences in nose and ear shape can go a long way in making mammals look distinct from each other, so I’d try to avoid doing the classic triangular cat nose.
Plus they both have those bony flanges on their lower jaws that machairodonts lacked.
Nimravids have slightly longer snouts and smaller nasal cavities, and being very basal feliforms I’d give them more “generic carnivoran” features based on relatives like viverrids and nandiniids.
Barbourofelids have rather deep jaws and a a sort of square-ish head shape. Their taxonomic position is a little uncertain – they’re either the sister group to felids or close relatives of nimravids – so I could potentially push their appearance even less cat-like, too.
As for bear-dogs… I did actually illustrate a couple of those for a PBS Eons episode a little while back! I’ll be showing them off here along with a few other images very soon.