Hypothetical - Cheap 360 Magnum Rebuild
The windage tray hp advantages show up on the big end. (High RPM's.) So, is there a bennifit to having one installed even though you do visit the high end often?
IMO, yes. It does help keep the oil under control and away from the crank where it can get pounded by the crank. It helps extend oil life and break down since it is not getting an extra beating by the rotating assembly.
It is a minor thing. But every little thing helps. Mopar stated it frees up 15hp on the big end. It also helps with mileage, albeit a small amount as the oil isn't hindering crank rotation. Also as well as oil life extension is also a small amount. As I mention above.
As far as how well the money you spend is done and how well it is, doing you best in the ignition vs. money on the windage tray is a cheap enough expense that both should not be an issue to spend on.
If it is, and you had to choose between the two, I suggest a second job and get both.