Button fired Pto engagement....

[Avenger]

When this happens to me, I try to 'bump' the PTO by turning it on and off quickly. Sometimes I get lucky.
This happens when I hook up to the rototiller, since the tines are on the ground. If it doesnt line up after a bump or two, then I pick up the implement and see if I can rotate it. This wont work for your situation.

The prybar might be your salvation.

Question about the pump though, does it have a bleed or anything that you can use to take the pressure off the pump/pto shaft that would allow you to spin it easier?

 

[spruce Deere]

All tractors with this elec. over hyd. Pto should all have a 'neutral'. I need to try your 'quick bump' trick avenger..... The jacto cannon sprayer does not have a pressure relieve on the pump. I did not try the pry bar on the sprayer shaft yet. Most of that resistance comes from a rather large impeller fan that creates the hurricane force wind for the sprayer.
When I was initially mounting it on the tractor the control lever was my main concern and most of the evening time I had went into that... Which took a longer trial and error period than I anticipated

I park my tiller on two pieces of 6x6 treated post left over from the shop lean-too build. There about 2 foot in length and placed under the skid shoes of the 60 inch kk tiller. It still wants to rock forward and I still have to use the tillers 'kick stand' but it sure is nice for mounting, cleaning and keeping it off of the ground.