Questions: How often have you done this before? Have you gone and asked someone with more experience for tips and ideas on how to make it easier? Have you trawled the tractor forums looking for advice? Or are you a new user of a developed technology with 50+ years of service who has immediately decided it sucks and needs rethinking?
I personally agree with you that PTO couplings suck; hydraulic drive is a lot easier from a user perspective, but there are a number of tricks to make handling the job easier. Grease the pins, never drop an implement on the ground but leave it on a pallet you can move, etc. A winch on the tractor can be very useful, especially with a pulley or two on the ROPS.