Re: 1969 evinrude 55hp model 55973
They come off easily most of the time, if you have the right puller. You can purchase a multi-use puller from OMC/BRP (flywheel & one piece gearcase), but they are a bit pricey. Most people just buy a harmonic type puller from a local auto parts store.
Don't use anything but a harmonic type puller though. Gear pullers and the like are likely to break your aluminum flywheel, which must be pulled from the center, not the outer edge.
Also, be sure to use Grade 8 bolts of the proper size, thread count and thread depth. Failure to do this can result in broken bolts and stripped threads in the flywheel.
As TD said, the hydro-electric shift systems are sort of a mixed bag. They can be just fine, or they can be a bit of a problem because of parts availibility. The last time I looked, the shift switches are NLA, as are the lower solenoids. The wiring harness in the midsection is also NLA. That said, I have a '72 65hp (same shift as yours) which has been a really good motor for me.
Here's an analogy that will surely get me in trouble with the "PC" crowd - hydro-electric shift systems are like women. If they have been treated well and maintained properly, they are a delight. If not, they tend to be very cranky and expensive.
Service manuals are available in a number of places. You can surf online or go to EBay. I bought mine at EBay for about $15. Don't bother with the aftermarket manuals - they try to cover too many motors to be of much use.