Have you cleaned the wheels lately? Track? Though "stainless" it doesn't mean impervious. It's a general comparative statement among steel types.
Electrical grease may halt or increase conductivity.
Most "dielectric" grease seals from moisture and is non-conductive by design, but the seal usually helps long term conductivity simply by prevention of oxidation and corrosion, even slight. Silicone usally, so anything it hits will have future painting/glue issues. If on a porous surface you won't get it all out..ever.
If you want one than encourages power flow. "Conductive" would be the keyword in the products description. Use very sparingly, messes aren't a good idea at all. Metal impregnated last I saw one.
The only issue I saw with the machine screws in the rails side, was one I couldn't see That would be the other side, and the screw being too long, and/or too high (note the angle) and cause deep pizza cutter wheel flanges, to hit the screws threads. I'd go straight into the rails footing for the "flat". The curves in the rails side will also not hold a connector as well for its connection, or for long term screw fastness (won't come loose as easy on a flat surface. Crushing the connector to shape helps, but it's still not a flat, so the screw head isn't seated correctly now)(we all have our own compromises we'll accept. It is a very tidy connection )
Z1000? 100w...seems iffy off hand, especially big loco's, but can motors and command? It might be fine? They run on less amperage than P.War in general.
MTH fans know a little better what it can and can't do But a PW 90w 1033 would be at its limit for many PW trains on that size layout.
Nickle silver track- Being new track, offhand I'd think the 100w would be just enough, but I think NS track might also have more resistance per foot than regular track..? Drops with copper wire can overcome that flow issue if it does.
The plugs added here or there (molex or other brand) is a great idea. If nothing other than to have "instant remote throttle" for testing here or there. Throttle nearby as well as the "cab remote" is nice when your frustrated and trouble shooting(an eventuality for about 90% of us by my guess)