Congratulations! Nice starting point (I also have a first month O, close to your number!)
Let me take a stab at your questions...
1. Likely worn out clutch, check linkage and bearing for wear, doesn't sound like it is releasing, something bent, worn or out of adjustment, or even stuck to the disc. (look at manual for how it works and how to adjust it)
2. Yes, two position switch (off/on) and the push button to start (looks like the old time car light dimmer)
3. Your S/G looks like a Wheel Horse one, likely turns "backwards", I would get the correct S/G (it would have oil cups that early), may need to locate correct brackets, but are easily found.
4. I would replace it, several good choices, I have used Porch Elec. for Cubs, great quality, fair prices, several other choices, Brillman, and I have seen someone on the forum mentioned making a good quality one.
Take your time, get familiar with it before you jump in and you will enjoy the refurbish experience!
Good luck,
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David
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