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Phineas, when you rebuilt the carburetor, did you adjust the float level on either float? If they are wildly out of adjustment or stuck, gas will not enter the carb. Odd that the fuel system is not staying pressurized. When you crank the engine over to start it does gas enter the filter and does the engine start?
The leak is likely not gas but oil as previously mentioned. Likely an oil metering pump or pump line leak.. possibly a front cover leak.. Clean the netering pump area and lines with brake clean and dry it. After this start the engine and run it and check for an oil leak there.