I have a 1923 model T, when starting with starter
The bendix gear should slide in and out on the drive with no resistance. I would suggest you try cleaning the drive well and make sure the counterbalance on the gear is not loose or broken free from the gear. If you throw the gear in and out on the drive, it should not hang up on either end. If it is hanging up, see if there is any burrs or something causing a bind.