Further troubleshooting: took off the filter and cleaned inside. Trying to see if oil will come out of the open filter cannister to check if there is a clog in the line from the tank into the house. No oil is coming out while the shut off valve is in open position, even when hitting the reset button. Oil should be draining into the can in the attached picture correct?
UPDATE AGAIN: Is it a truly awful idea to try to siphon some heating oil out of the bleeder valve using a pump?
FINAL UPDATE: after taking a really careful look at the bleeder valve, it turns out that there I was unscrewing the HOUSING that the actual valve sits in, not the bleeder valve. Unscrewed the actual valve and got it up and running in about five minutes.