The trouble is, many steels that are easy on the heat side, are demanding on the quench side, and many of those that are not too picky about the quench are picky about the heating.
For example, 1095 isn't too picky about being heated. It benefits from a brief soak, but a couple minutes is adequate. But the quench speed is very critical, so you're stuck using water (and risking cracks and warping), oil (and risk getting pearlite) or getting a good grade of fast quench oil (and risk, well.. nothing actually)
O1, another "easy" steel is easy to get it to skate a file, and you can quench it in about any oil (I have even used chainsaw bar oil) but it really needs a decent soak at temp. It takes at least five minutes to get all the "stuff" dissolved and evened out. I soak it 15 minutes once it reaches temp.
So, both of these "easy" steels are easy to skate a file, but actually require some skill to do well. Most steel is like this, having some aspect to it that requires skill or equipment to ht well. The exceptions are the low alloy, moderate carbon steels, as already mentioned.
Due to the low alloy and moderate carbon content (which reduced the need to soak) and manganese (which widens the quenching window), 1084 needs no lengthy soak, and any reasonably fast oil is good enough - so I'd say that 1084 may be the easiest to HT.