After stripping the original finish this is what you are left with.
The next step is to mark a layout line in the center of the flat on each side. The line should follow the curve of the flat as seen in the pic. You will shape the front and rear of the tote to this line. The goal is to shape the cross section to an elipse. Be sure to make the front and especially the rear radii as blunt as possible otherwise it will be unconfortable to push this tote for long.
This is the simple jig I use to hold a tote for shaping. The threaded rod is 1/4-20 and the angle is 26 deg. for #3 and #4 and 27 deg. for #4 1/2 up.
I use a Nicholson #49 cabinet makers rasp, a Nicholson 10″ half round bastard cut and Nicholson 8″ half round smooth to do all of the shaping. Move the files and rasp in an arcing motion to minimise the facets. The object is to remove the flats on the sides not change their angle. Take you time and work slowly feeling the arc with your fingers. File until you have a smooth arc. You can always remove more material. The files will do 90% of the shaping. If done well you can start sanding with P100 or even P120 paper.
Here the tote is in position to begin rasping the front. When that is done rotate the fixture 180 deg. to rasp the rear.
Next move to the rough and fine files. Again work slowly and carefully. You want to do just about all of the shaping with the rasp and files, not with abrasive papers.
This is what your tote should look like when you are finished filing. Next clean the center at the layout line by moving the 8″ smooth file in an arcing motion lightly over the layout line to clean it and fair it into the tote.
This is what the tote should look like after shaping. All that is left is the sanding. I start with P100 and move through the grits to P400. Then apply the film finish of your choice. I don’t recommend an oil finish. A very smooth film finish feels better in your hand after a couple of hours of pushing a plane.
Here you can see that I kept the back of the tote as blunt as I could given it is only 15/16″ thick. I make my totes 1 3/32″ thick and they are very comfortable to use.
For comparison the reshaped Stanley tote is on the left and the R & B tote is on the right. The Stanley is 15/16″ thick and the R & B tote is 1 3/32″ thick. This extra thickness and a little extra height make a big difference in the feel of the handle. The R & B tote is still comfortable after a long planing session.