I was planning on using my hf blue pump to feed two outlets in the tank;
The first is roughly mid/lower oil level and the second is through the small bung on the tank top.
The supply pipe is 3/4 black iron and I have adapted it down at the end to 1/4 pipe.
The piping runs vertically from the pump, teed to mid port then up and into the top port
My questions are;
Will the pump supply the 2 ports and will the oil volumes be equal?
This is on my 55 gall cone bottom tank
Thanks,
Andrew

If you run the bottom one with a smaller diameter output then the back pressure will force volume through the top port providing it is of a larger diameter outlet seeking the path of least resistance.

Yes a no mm maybe, it has been many years since I have done it but there is some math you can do to work it out. Based on the pressure developed by the pump and the friction in the pipe you can determine the flow. If the flow through the large pipe is in excess of the flow through the smaller pipes it should be okay.
If you searched Google for irrigation setups or similar you should find all the data and probably online calculators that will work it out for you, treat the small pipes as nozzles.

The density of the oil will vary based on the temperature at different heights of the column you are draining. Cooling will happen from the bottom to the top and from the outside in. The oil will contract as it cools after it is drained, until it reaches the current room temperature.

Assuming that since you are in Vermont you have arranged to heat this oil so it will flow in the winter months. As for now, if you are just using natural sunlight to heat a container of oil, the same rules apply - the oil at the top will be thinner since it is warmer.