Wrong, wrong, you are all wrong!
A brand new oil pump will (should!) produce such a strong vacuum that you can even 'distill' frozen water. This is known as freeze drying. The final vacuum value you determine by distilling water will be too high. Most likely you won't be able to distill the water anyway, The vapors will simply be sucked through the pump.
When distilling toluene the same will happen, except that the tolly will dissolve in your pump oil which means you won't get the full vacuum again until you change the oil.
The new pump will most likely make sassy boil around 60°C. That temp is too low for 100% vapor condensation without a very efficient cold trap, so some of the more volatile components (and also some safrole) will end up in your pump oil.
All organic solvents and compounds will also dissolve in the rubber tubing you are using, and will slowly gas out of it even when they are not present during later distillations. That's one of the reasons why rubber tubing is not advisable if you want a better vacuum than 1mbar or so.
A $10 vacuum gauge is completely useless, all it can show you is whether the pump is running or not. These devices simply lack the necessary resolution at the lower end of the vacuum, you can guesstimate pressures like 200mbar or 700mbar with them, but they won't be able to tell you the difference between 0.2, 2 and 20mbar.
The final pressre of the pump is strongly dependent on what kind of equipment you are using, how clean it is, and how it is connected to the pump. Even the most expensive pump will not be able to reach its final rating as long as highly volatile (low boiling) stuff is present, the tubing used will let gasses diffuse through it, the diameter of the tubing used is low, and it's not given enough time to reach its final vacuum (which might take hours). It might reach a vacuum suitable to your purpose, but that value might differ greatly depending on exactly what you are doing and the condition it runs under.