This is just some of my thoughts that have popped up over the years when reading the countless knife sharpening threads. This is not meant to offend anyone nor discourage anyone. It is just my opinions and experience.
To get good at it you have to practice. I don't think there is a sharpening system made yet where you can skip that step. So toughen up. Sore fingers are part of the game. As is ruining a good edge, cutting yourself, getting dirty fingers and getting let down by some magical sharpening system. Sorry. There is only one shortcut in my world. It is right at the end of this message and it is called stropping.
Get a cheap and medium sized knife from anywhere cheap. Practice on that. Change the angle to a solid 30 degree and down to a skinny 8 degree or anything in between and each time go out and try that knife. You will find that you prefer one over the other. And that is allright! You don't have to have an exact 17 degree something on you blade. Even if your favorite youtube knife hero says so. Maybe 22 fits your use a lot better.
Get a cheap and small knife. Repeat the steps. New angle. Maybe a new profile alltogether. I've changed the blade profile completely on a few knives after the tips broke off. Did the sharpening on an ordinary carborundum knife sharpening stone. The square one. One side is fine the other coarse. Takes some time but unless you chose a psycho hard steel knife to try it on then you will get it done sooner than you think. (But not as fast as you may wish)
Get a sharpening steel. Now learn how to use that. That'll keep most of your knives tip top most of the time. Dont buy a diamond one. Those are for removing material. Steel ones are for straightening the edge. If a sharpening steel does not produce a super sharp edge in 20 strokes or less you go back to the stones/abrasive paper/fancy machine and try again.
After you learn to use that sharpening steel you can keep you pocket knife scary sharp most of the time by sharpening it on just about anything. Adjustable wrench, spanner, screwdriver, a glass bottle, a shovel, the back of another knife... You name it.
Get a cheap piece of leather. Forget those expensive strops. Because if you upfcuk just once when stropping... you cut that strop halfway through before you can stop your hand... Ask me how I know! (Mine was an old leather belt where the buckle had broken... Phew. But still)
Get "something" put on that leather strop. I don't care what it is called. 790000 grit fairy dust? Fine by me. Just get something. It makes a difference. But once your knife is really sharp it will hardly need the strop. But stropping it till that last fine edge is a lot quicker than doing it any other way. I have used the carborundum paste we use to grind engine valves. The finer one. 400 or 500 grit if I recall. And dont use a whole lot of abrasive paste.. Wet the leather with some oil. Does not matter what oil it is. Then apply the paste.
I am by no means a master at sharpening knives. But all my kitchen knives are shaving sharp. My 3 dollar 2 inch pocket knife cuts 1.5" reinforced rubber steam tubes with little effort. I practiced a lot.
EDIT: Some things I forgot..
Ever wonder when it is "good enough" ? It is when you touch the blade to your fingernail at an 90 degree angle and try to gently move it sideways. If it "bites" in to your nail and does not want to move or if it scrapes the surface off it is good enough! (don't push on it, no pressure! If it is scary sharp it will cut through that nail before you even think about it.)
Many cooks use this to assess if their knives are sharp enough after a session with the sharpening steel. Why? Because if they tried the shaving then there would be hairs in the soup! (An actual cooks joke . At least it was a cook that told it to me when discussing knives and sharpening)
Best fixed blade knives are Mora knives. For the money and in any situation I've had to deal with. Can be as sharp as you like. Can take a beating. Comes with orange handle so you can find it again if it ever goes anywhere outside with you. These can be punched through a kevlar plate. I don't need anything else. About 8 usd here in Denmark.
Best daily folder is Opinell. Nothing fancy for the money but can become scary sharp on the flat side of a small rock in 1 minute flat. Comes in all sizes. Illegal to carry here in Denmark due to the lock. So I carry a 3 usd noname folder.