That all depends on the parts you use. Some kits run on injectors just fine while others will seize almost instantly.
One thing to consider is the pump supplies varying amounts of oil. At wot it is around 50:1. Adding oil to the tank at the same time will LEAN the fuel charge creating more heat in the cylinder. As you let off the throttle your pump goes down to around 100:1. With the same lean fuel (in the tank), and the heat from the wot run you are now decelerating at lets say 8'000rpms with an Approx oil mix of 90:1. More heat
I talked with a top notch tuner about this, and I tend to find him correct. "If you are running a higher power output engine than the pump was intended for USE PRE-MIX."
I ran a Malossi kit for almost 4 years on the pump, and added about 1/2oz 2t to the tank. I can't say your set up WONT work but I have since been staying with one or the other.
In fact the Malossi was on the FIRST engine I have EVER left the pump on. Injectors are easier but not always better.
To answer your first question... When you pull the cylinder off you will know by the condition of the piston rings if your oil is a good choice. They should still fit loosely in the grooves, and not be binding. There should be NO deposits in the groves.
Post a thread on your build! We'd love to see it.