I have been sharpening my saw chains for 30+ years and lately most of the time I can get them to cut pretty good. Not so when I first tried and for quite a while after.
The top angle is the most critical issue other than getting all the dull out of the tooth. Most of the time attention is focused on the point of the tooth and not the other side, or open side, of the top of the tooth.
Look closely at the tooth profile of a new chain and try to keep the top angle and side profiles the same. There are two angles to the top on the tooth, one you see looking down at the top of the guide bar the other is what you see when looking at the side of the guide bar.
When looking at the top of the guide bar the alternating angles of the top of the teeth can range from 25 to 35 degrees. an angle of 30 degrees is fairly standard some chains will have a line scribed on the top of the tooth near the back that matches the angle the cutter was originally sharpened to. (The manufacturer says this mark is to tell you when the chain has reached the end of life.) Keeping this top angle consistent will help keep the saw cutting straight.
The top of the tooth angle looking at the side of the guide bar wants to be fairly blunt, more vertical than horizontal. The more horizontial this angle the thinner and longer the cutting edge is and will dull quicker.
The profile of the side of the tooth will have a slight hook to it, try to keep this profile. More hook affects the angle of the top of the tooth.
The raker in front of the tooth controls the depth of cut and is very important. As the tooth is filed the relationship between the raker and the top of the tooth changes, the tooth becomes lower than the raker. Usually a height difference of .025 ( 25 thousands of an inch) is standard. Those who have what is called a safety chain or low kick-back chain will have another piece in the chain that sits in between the raker and the back of the tooth in front of it. I have filed those down also to make the chain cut right.
The height of the raker will greatly affect how the saw cuts. When the raker is too high it will feel like you have to push the saw through the wood and the saw dust will be little short pieces like dust. When the rakers are too low the chain will grab, bounce, and bog the saw down. The saw dust will be thicker and chunky but still shorter. When the rakes are near the proper height the saw will cut smooth and slightly pull itself into the wood without bouncing. The saw dust will be longer curls.
When trying to "plunge" or bore with a chain saw start with the bottom of the nose of bar and feed the bar in until the round of the nose can not be seen. At this point you can begin to rotate the bar to plunge straighter in, BUT REMEMBER TO KEEP MORE PRESSURE ON THE BOTTOM OF THE BAR. Once you have either come out the other side or have burried the bar at least 3/4 of the way in don't think of cutting with the top of the bar.
If your raker height is too low and you are trying to make a plunge cut it will be uncomfortable and dangerous no matter what you do.
Be safe.
Randy