> It seems to be working fine
Here's the deal. Ideally you measure the different temperatures: transistor, heatsink, air. If the transistor is under 75 deg C (hurts the skin but does not raise blister), go worry about something else. If hotter, see if the bottleneck is transistor to chassis, or chassis to air.
BUT DO NOT stick your finger on a 400 Volt device!!
Put a teeny drop of water on the epoxy case, so it won't roll onto the leads. Cook for a few minutes. Depending on the amp and the VVR scheme, worst-case may be half-loud and working very hard. If the water does not boil, the transistor will probably last forever.
IR thermometers are handy for non-lethal temp checks. Just note that cheap ones "read" a large area. If you have a hot-spot, you have to get close.
If the transistor IS recklessly hot: compare transistor to heatsink. If these two temps are very different, you need "better contact". Flatten the heatsink surface. Get some torque on the screw (but do NOT cut the insulating washers!). Grease is a final step -after- all other details are optimized.
A plastic "TO3" flange on a sheet-metal chassis, if the device-chassis joint is nearly-right, the BIG problem is that sheetmetal won't carry much heat. Super-polishing and silver-greasing the transistor is not going to change that.
On a thin steel chassis, heat conduction is pretty poor. Your beefy aluminum can carry-away many Watts safely. Grease is probably not needed.
Grease IS needed when you have many-fin 1/4" HEAT SINK, and need to get full use of the expensive sink.
Grease is useful on modern PC CPUs with many-many fanned fins. The cooler can pull heat out fast enough that the metal-metal joint between CPU and sink becomes an impediment. Hot CPUs may run 10 deg C cooler with careful grease. OTOH, they can run 50 deg C hotter if you get a speck of crap between CPU and sink. Done that, had the instant shut-down. The crappy "clamps" on the current Intel CPU heatsinks are very prone to bad contact.