I have placed electric fuel pumps on my supers and it has taken care of the same type of starting issues that I had as the carburetor is now full of fuel before attempting to start. Also I always bring the throttle up 1/3, start cranking the engine over and after it gets up to speed (3 seconds) then pull the choke out until it fires, then partially push it back in and they usually take off and start.
When it's cold out everything plays a role. I assume you have good gas (not some from last summer), the battery is strong and winter oil in it. When it is running and the hydro is in neutral (no brake on) does it sit there or want to move? If it moves a little forward or back it needs adjusted or it will drag when starting the engine.
Basically with a centrifugal type starter drive, once the engine fires once and does not continue to fire and start, the initial cylinder fire takes the load off of the starter and the engine will throw the starter drive out. It's a common problem especially in the winter and is why most starters now have a solenoid to hold the drive in. Hope some of this may help!
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