Re: is working on a 55 fastwin diffiuclt?
well before you call a mechanic, who probably will not even work on your old motor, let's try a few other things. For starters the grinding sound and the not starting are alost certainly two separate issues. The motor can run without the lowerunit and essentiall does so when in neutral.
When you drained the old oil, did you notice any large chunks or fillings of metal in the old oil? If so, you may have chipped/worn gear. However, if it ran smooth prior to the gear oil change we shold be able to get it to do so again. When you're changing gears are you doing so quickly or gently? Outboards like quick, assertive gear changes. Don't try to "ease" it into/out of gear. Can you shift into gear smoothly when the motor is not running? You shoudl be able to. You may have to spin the prop a bit by hand to help it to slip into gear, but it should do it. If you turn the flyhweel CLOCKWISE by hand, can you see the prop spin clockwise when in forward and counterclockwise when in reverse? Also, doubel check the shift rod connector. It is tricky to put back together and may cause poor gear shifts. The shift rod connector is behind the the little, oval window on the side of the leg that you circled in red in your first photo. The two rods must be fully connected for proper gear changes. It can be tricky, so don't get frustrated. take your time. there are also lots of posts here in the forums about it.
As for the not starting. There a three things you need: fuel, spark, compression. If you haven't done anything to the carb yet, then we'll assume it's still ok. However, are you sure you didn't turn any of the knobs/needles on the front of the carb which say Lean/Rich, if so, return them to the position they were in when they worked last. You can do a very crude check for spark by removing the sparkplugs keeping them in the s'plug wires and resting them against the metal body of the engine. Pull the flywheel and you should be able to see a bright, blue spark, which makes a snapping sound. Again this only a cude test, but it will give some good info.
try these tricks and let us know what happens. stick with it you'll get her going. this is how we all learned about our motor. besides this all part of the "FUN" of owning the older motors

While it may seem frustrating now, you'll be glad you stuck with it, and in time, you'll be able to fix almost anything on theses guys witha few simple tools and some know-how. Keep us posted. Pics are good.