I could never become adept at filling a tube with water/sanitizer to start the siphon. It would always take several attempts and I would make a mess. Maybe I need to watch someone do it on YouTube or something.
I use an autosiphon. I clean it and my tubing by doing a PBW soak using a wallpaper tray, then a StarSan soak in the wallpaper tray (I know you don't need to soak in StarSan, but it is easy to immerse it in the tray while I do other things.
It's not too tough really.
1 - Lower your tubing into a bucket of sanitizer ensuring that it is filling completely
2 - Attach one end to the racking cane and cover the free end with your thumb
3 - Put the racking cane into the fermenter and the tubing into a pot or pint glass
4 - Release your thumb and watch science happen right before your eyes.
5 - If steps 1-4 fail, take a swig of booze and start the siphon with your mouth.
When I used this method I dump into a pint glass until all sanitizer was free, I then pull an additional 8oz for testing and tasting.
I only used this method when fermenting in buckets.