Unfortuately, most home stand mixers, like the KitchenAids, can't do as good a job with dough as a Hobart. So, you have to play around with the machine and the processing. Some people spray the dough hook with a light oil spray (you may have seen Alton Brown do this in a foodnetwork segment), and some will use the paddle attachment to get a good start. I have noted at least four places where human intervention in the process is quite often needed.
First, is to get the dough ball started. The flour will often spin around the bowl and stick to the sides of the bowl. I use a spatula to scrape down the sides of the bowl to direct the flour into the path of the dough hook or paddle. If necessary, I stop the machine to do this, but more often I am able to do this while the machine is running (at low speed).
Second, is the hydration issue--the one you mentioned. Instead of throwing the entire amount of flour into the bowl at one time, I add it gradually, using either the stir or #1 setting, and, if necessary, the spatula, to keep the flour and dough in play. You will have a better chance of incorporating the flour into the dough ball that way, even at relatively high hydration levels up to 65%. If you decide to use an autloyse rest period, that will also improve the hydration.
Third, is kneading in the oil. When everything comes together in a rough dough ball, that is when I add the oil, and knead that in, usually using the #2 setting. If the dough ball sticks to the dough hook or it doesn't seem to be incorporating well, I just stop the machine, do a little bit of hand kneading (which itself will also improve the hydration of the flour), and put the dough ball back into the machine and resume the kneading.
Fourth, is the matter of adjustments. I usually do this after the oil has been added since it is a liquid and will absorb some flour. My experience is that where the flour and water have been weighed on a scale there is usually not much need for any adjustments. However, when adjustments are called for, I do it a teaspoon at a time. Many people make the mistake of adding too much flour because the dough seems to them to be too wet. I have found that just kneading the dough by hand will reduce that wetness by a surprising amount. It is only when you can't remove the dough from your fingers after hand kneading that you may want to add a bit more flour. But only the minimum--like a bit of bench flour. I want the dough to be tacky.
I might also mention that fellow member Friz has found it useful to use a high machine speed (I think is is above the #5 setting) to get a high enough centrifugal force to propel the dough ball off of the dough hook when it is riding the dough hook. Sometimes jogging the dough hook by shifting from one speed setting to another will also help dislodge the dough from the hook. But I wouldn't recommend using the high machine settings for too long a time, for fear that the dough will develop a close crumb in the finished crust because of overkneading. The final thing I do when the dough ball looks done is to knead the dough by hand for an additional minute or so. That helps shape the dough ball into a nice round ball but it also gives you a good idea as to whether you succeeded or not in getting a good dough ball to proceed with. That is also the time when I weigh the dough ball (mainly for my notes) and take its internal temperature to see how close I have come to hitting the 80-85 degree F finished dough temperature.