What do you all do when you are going to multiple different airports using IFR clearance/flight plan?

Normally if I need to file and am stopping at more than one airport, I file for each leg. One time I filed from my home airport to my home airport via another airport and that seemed to screw everything up with the controller. He worked with me and I think that since I was only doing a touch and go at the other airport it was easier to make it work. It was obvious that this wasn't the way he wanted to do it though.

So say you are going from XYZ to ABC to pick someone up then taking them from ABC to XXX and dropping them off then back to XYZ to end your flight. Just enough time on the ground to pick up and drop off. My thoughts are to just file to each airport then pick up next clearance before departing each time. Any other ways to get it done that are easier? Normally I am just A to B and don't have to give it any thought but I have an Angel Flight coming up that I will need to go pick the person up, drop them off and then go back to my airport. Just want to do it the right way.