If the can is plumbed back into the sump there wont be any funky stuff going back. The oil will just do a loop, though if everything is setup correctly you wont need the drain anyway, thats just a bandaid fix/precaution. Other thing I forgot to mention is to have atleast 2 x big breathers on the can, atleast 32mm inlets. You want the can to not become a restriction, needs to be free flowing.
Oils are up in the air. Some people run synthetic, some run semi and others straight mineral and have no dramas oil wise. You would have to do constant oil analysis reports after every track day to see how the oil is handling the load and slowly breaking down to find out which one works the best with your setup (you might find a cheaper semi or mineral oil will be fine for your engine). More often then not most people change the oil after several track days anyway, even though the oil is still good enough to keep using(usually just out of precaution). Why spend big dollars on oil that is changed frequently when a cheaper semi or mineral oil will work fine with the same short intervals. The cost of oil adds up quite quickly, even more so in race cars when you have big sumps with oil coolers and external filters with -10/-12 lines everywhere adding more capacity to the system, quite easily upto 10L, so you need to buy double what you usually would. The top end synthetic stuff is already stupidly exxy and some of them arent even compatible with E85 which is quickly becoming the fuel of choice for track cars. Do some research and look into it before buying the most expensive oil you can get purely because you think it will be best for your specific setup.