I always plug the centre hole and run a drill a bit smaller diameter then keyway size through where its is going. Drill running half in the plug half in the part getting the keyway.
Shifts most of the material so the key cutting bit or broach has less work to do. Few strokes of a file to clear a bit more out of the corners too.
Makes big difference to the effort needed, especially if planing on the lathe, which is good thing when using improvised methods. If planing on the lathe with a boring bar arrange some sort of support for the bar immediately in front of the work to combat deflection. Adjustment can be a right pain but it seriously reduces the chance of deflection as the cutter enters the work.
The art with this sort of planing job seems to be to get a good clean entry with the cutter working nicely. If you get the angles right there seems to be an element of self stabilisation under cutting loads helping against deflection. My experience is that with a relatively long keyway, where deflection is most likely to be an issue, if the first half or so goes true the back seems to follow just fine. If you have issues close to the front the job turns into a right battle with lots of scraping cuts to get the taper out.
I’m certain there is an art to getting planing speed and cut depth balanced.
As ever for me third time was the charm! First couple of efforts were, ahem, “seriously disappointing after all the hard work and verbal encouragement”. Penny dropped on third go. Later I bought a broach set which is much easier. I do think the planing experience helped with the broaches tho.
Set something up and practice. It really isn’t that difficult but you do have to dial in the feel for the job.
Clive