I take it you have an earlier style car? If so, the starter is a sore point on them, because it doesn't have a proper follow through whatever the technical term is. The later starters are much better. The earlier cars tend to disengage. It almost sounds like you are getting too much fuel as you said. There could be something going on with the carburator or needle and seat, so just for the purposes of getting it started and running if it is flooding (and it isn't not starting because of bad old gas,) maybe disconnect/divert the gas supply until after you have got it started however briefly. If it is choked properly, try getting to run with a bit of starting fluid and followup a second time with a bit of gas in the carb. I try to work the linkage to get it to accelerate on the existing fuel in the carb. Every bit of running will make it hotter in the cylinders and more likely to fire the next times even with low compression. If you get it to the point where it will run a bit, then reconnect the gas line, and keep it running as long as possible, and pour a prepared mixture of 50/50 new gas and Marvel mystery oil bit by bit into the carb as it is running. Keep the revs above idle, and goose it a bit. The heat and pressure might ungum things a bit to raise the compression a bit--every bit helps the next time. If you get it to the stage where it heats up to operating temperature, and can idle, then I would adjust it to a fast unchoked idle. The oil in the gas will make it smoky, so if you can do this outdoors...
After this sort of treatment, I like to change the oil after a good half hour or so of running time while it is still hot, and put in fresh, and start it up again to repeat. With my Studebakers, they are sometimes reluctant to start if they have been sitting for a month of more (they all have un-rebuilt engines, but the Kaiser was rebuilt some years ago) and smoke and drip oil, but the more they are run the better they get.
