Tiling around my shower and tub was a pain, but by far the most challenging part has been the caulking. It has been a real mess! I have tried using tape to create a smooth line, however it is not perfect and leaves a harsh line. To avoid this, I use less caulk than necessary and then use my finger to pull the extra caulk to the area I am smoothing out. This way I get the exact amount of caulk I need without the mess. I have done this multiple times in about 50 to 60 bathrooms and it has never let me down.
I understand that caulking can be a difficult task for perfectionists, but my best advice is to have confidence. Before beginning, make sure that the surface you are working with is prepped and there are no surprises that will disrupt your caulking process. Mentally rehearse what you will do before you start and adjust slightly if necessary. With this approach, caulking becomes a much smoother process.
I found that watching a tutorial video on caulking helped me. Seeing how it is done in real-time gave me the confidence I needed to succeed. With enough practice and experience, caulking can become an easier task.