Sharpening gets treated as a dark art and it is not. An edge is simply the line where two flat surfaces meet, and sharpening is making both of those surfaces flat and smooth enough that the line between them is fine. Everything else is detail.
Flatten the back first, once
Half of the edge is the back of the blade, and a back that is not flat cannot produce a sharp edge however much work goes into the bevel. On a new or old tool, flatten the first inch or so of the back until it is uniformly polished, then never touch it again except to remove the burr. This is tedious and you only do it once per tool.
Honing versus grinding
Honing refreshes the existing edge on a fine stone and takes under a minute. Grinding reshapes the bevel and removes real metal. You hone often and grind rarely.
The test is the edge itself. Look at it under a light: a sharp edge reflects nothing, because there is no flat surface left to catch the light. A dull edge shows a bright line. If that line is thin, hone it. If the edge is chipped or the bevel has become rounded from many honings, grind it back.
Why it goes wrong
Rounding the bevel is the usual fault, caused by the angle wandering during honing. A honing guide removes the problem entirely and there is no virtue in freehand work for its own sake. Rocking the blade is the other fault, and it produces an edge that feels sharp in the middle and does nothing at the corners.
Overheating is a grinding fault: if the blade discolours to a straw or blue tint at the edge it has lost its hardness there and will not hold an edge again until that section is ground away. Grind in short passes and keep the blade cool.
Remove the burr
Honing leaves a fine wire edge on the back. A couple of light passes flat on the stone takes it off. Skipping this gives you a tool that seems sharp for the first three cuts and then is not, because the wire edge has folded over and broken away.
How often
Far more often than feels reasonable. A chisel being used continuously in hardwood wants honing every twenty minutes or so. People resist because sharpening feels like an interruption to the work, when actually the dull tool is the interruption: it tears rather than cuts, it needs more force, and it is considerably more likely to slip.