Joe and Tim, what you guys describe makes sense, so I can rule out levelness as an issue (Houston is pretty flat so I don't normally think about hills..).

I'm just getting my feet wet in carburetor tinkering, and wanted to know if levelness could contribute any to leaks or carb issues. After poking around I've found that the leak is likely a bad needle/seat, leaky float, warped carb top, too much fuel pump pressure or some combination of them (maybe an issue with gas tank venting?). I don't think my fuel pump is putting out too much pressure as it is just the stock mechanical glass bowl unit that I rebuilt with a new diaphragm and spring.

I'm planning to rebuild the carb, replace the float/needle/seat and see if that fixes the leak and my hard starting issues. I've ruled out ignition as the hard starting issue since I've replaced all of those bits, set the timing and it starts/runs no problem only after I dump a little gas down the carb.