Glad you got it working.
I measured the current between the input and the resistor and it was slightly above 1.5v.
If the result you got was in volts the quantity you measured was not current.
thought that a higher resistor would limit the current much more than a lower resistor,
Yes it does. What you are trying to do with that sort of logic is to suck current out of the input to get a logic low. With the higher resistance you were not sucking enough current to make the input voltage drop below the threshold for a logic zero.