It is a common misconception that the liquid to gas transition is an abrupt process that happens suddenly at the boiling point. The liquid is actually turning into a gas (and vice versa) at all temperatures, which is why wet clothes dry if we hang them on a washing line. It's just below the boiling point we call this process evaporation instead of boiling. It's true that boiling is "special" in that it happens at a constant temperature, but as we'll see in the moment the constant temperature is just because the process happens as a constant pressure and it doesn't reflect anything fundamental.
As a rough approximation the rate at which molecules escape from the liquid into the gas phase is proportional to the temperature of the liquid. The rate at which molecules in the gas phase recondense into the liquid depends on the partial pressure of the gaseous molecules.
Suppose we hang out wet clothes to dry in a closed room with initially dry air in it. Water will start to evaporate from the clothes and the partial pressure of water vapour in the room will increase. As the partial pressure of the water vapour increases the rate at which water vapour recondenses increases, and we reach a dynamic equilibrium at which the rate the water evaporates from the clothes is equal to the rate at which the water recondenses onto them, and the drying process stops. One way of describing this is to say the air in the room has reached 100% relative humidity.
If we increase the temperature the rate of evaporation increases, and as a result the partial pressure of water increases until we reach equilibrium again.
And so on, we can keep increasing the temperature and the partial pressure of water vapour increases to maintain equilibrium. We can keep doing this to arbitrarily high temperatures, well above 100°C, because the pressure can rise without limit as well. In this system the water never boils so there is no boiling point.
But, if we attempt this in the open air there is a limit to the pressure because the ambient pressure is 1 atmosphere. So when the partial pressure of the water vapour has increased to 1 atmosphere it cannot get any higher, and this happens at 100°C. If we increase the temperature of the water the increased rate of evaporation is no longer balanced by an increased rate of condensation and that's why we see boiling.
The point of all this is that you cannot understand the process by looking at a single molecule because single molecules are continuously undergoing the liquid to gas (and back) transition at all temperatures. The reason boiling happens at constant temperature is nothing to do with the properties of single molecules. It's because we have limited the partial pressure of the gas phase to a constant value of 1 atm.
Response to comment
In your question you say:
and perhaps to simplify things assume there wasn't a distribution to the molecular energies, they were all essentially at the same average energy
but you cannot make this simplification as a thermal distribution of energies is fundamental to the process. The energy required to remove an atom from the liquid to the gas phase is roughly independent of temperature, and the reason the evaporation rate increases with temperature is because the probability of any one molecule getting that much energy increases with temperature.
You ask:
if you gave a molecule an amount of energy less than the latent heat required for a single molecule to vaporize?
and the answer is that within a few microseconds it would have thermalised with the molecules around it and its energy would randomly increase, decrease or remain roughly constant. If it's the first of these it could escape to the gas, or if it's the second it could transfer enough energy to another molecule for that molecule to escape to the gas.
You really cannot understand boiling by considering just a single molecule. It is an ensemble process.