Thanks for the report, Salty. Please remember, do not prime the cylinder as a regular method of starting that engine - it will ruin it over time. It appears the starting problem is your choking technique. We can talk about that if you like, or you may want to pull the rest of the machine to pieces right away. It does sound as if your engine will be quite functional with a simple tune-up.
It sounds as if your cutter clutch is not freeing properly, which may mean it needs to be adjusted. Alternatively it may have an internal fault, such as the cork facing inside the clutch has been damaged. This is not difficult to fix.