2 oil fills on Troy bilt 5550 generator ?

Lawn Boy snowblower with Techumsa engine - 8hp I believe, maybe 10hp. Usual start-up procedure - choke on, throttle up and three presses of the rubber primer button. Third pull it started right up. Turned the choke back and it died. Nothing since. Plugged in to start with starter and just a "wwwhiiiiizzzz" Ok, so the starter is gone but nothing from pulling either. Perhaps I just never noticed but it seems there's an air sound from the muffler. No feeling of compression chnage. Pulled plug and it was black with oily stuff and a bit "gritty". Changed plug and it's a nice blue spark but still nothing. Priming gives a "sucking" sound from the carb area. Getting fuel to the carb as the float bowl will fill and drip. Not concerned with the starter as it's always pull-started easy. Probably 5 or 6 seasons of use. Thoughts?

My 5 hp Sears snowblower (model 536886440 - engine 143015005 Tecumseh, although it says Craftsman) wouldnt start, so I replaced the spark plug and then took apart and cleaned the carburetor. I left old gas in so figured that was the problem. When I reassembled the carb tonight and tried to start, the pull cord was almost impossible to pull, and then oil (not gas, but straight up black engine oil) started coming from the top of the carb, from the tube that the choke valve opens and closes at the end. Sorry I dont know the official name for these parts, as this is the first time I have ever attempted engine repair. I had the snowblower almost upside down for a couple of days from when I took the carb parts off until when I replaced them today, so I assume something bad happened during that time and the oil leaked into somewhere that it shouldnt. Any ideas why the pull cord might have seized up and where the oil is coming from or how I can stop it? Assume these are related and sorry for amateur hour - but could really use help before the next storm arrives.