I haven't done a 044 kit, but I've had good luck on the 660's just with checking first and breaking the edge on the "step" to the sealing surface if its sharp, then with a little oil it usually goes right through the seal with no strain or pain. Last two were rounded as delivered. I had warmed the case/bearing a little on the one in the video but doubt that had any effect. The first MS660 I built actually failed & the rubber rolled out, but the edge on that crank was knife sharp, so I started paying attention & rounding that edge. Also as with the Husqvarna 395's, the shop seal installation tool just puts support around the rubber sealing material, same with the Stihl MS660 seal install tool. They work fine, so I might turn a dedicated tool on the lathe to support the crank & seal as the Stihl shop tool, mount it to a base where I can set the case & crank on it for the press and just be done with it if folks keep handing me cases to assemble. To this point in time I have not had to use the sleeve method....but it too is a concept used by some successfully as well...
Just be careful that it doesn't have an edge that can damage the seal when it is removed.
But the worst case is.....you have to yank the seal and put in an OEM anyway, so where is the risk in just trying to push that crank through? Love these kits for fun and games....so little monetary risk, so much to be learned & fun to be had...
