In the summer when I ship out I make sure I have stalls done and everything set up for pm chores in the morning before work so when I come back I can just bring horses in, feed grain and be done.
I race home from work, load and go. The arena I ship to is about 7 minutes away. I will admit to speed grooming and tacking quickly. I ride 2 horses which takes me about 3 hours total door to door so to speak. I schedule myself with quicker rides on week nights, and spend more time on weekends. Horses get a better grooming session then as well.
Shipping out is doable, and if you are only doing it say one weekday and both weekend days it shouldn't be too bad.
For me I try not to look at how difficult it is and what a PIA it is, but just do it. It's like going to the gym. Once you get in the routine it is easy to keep momentum.
The difficulty is worth it in many little ways. My horses are all excellent loaders and shippers, I can hook up my trailer in one try....little things like that.