Recent attempts at sampling SMIRKS space highlights the difficulty in automating chemical perception. We introduced two tools, SMARTY and SMIRKY, which attempt to discover atom and fragment types using a Monte Carlo sampling algorithm. The foundational algorithm in these tools started from very generic patterns and created child parameters by making very simple changes to those patterns. Some downsides of this algorithm were straightforward, where perhaps a change in the type of moves could have lead to slightly higher success. However, the major takeaway, was the realization of the huge combinatorial problem when generating moves in SMIRKS space for parameter types with multiple atoms and bonds. In fact, we calculated that SMIRKY would take up to 1 billion moves to find SMIRKS patterns with the combination of decorators for certain torsions. To put this in perspective, a SMIRKY simulation of 100,000 iterations required over 700 CPU hours. This is largely due to the chemically naïve moves in SMIRKS space choosing new decorators for atoms and bonds at random with no concern for what combinations make chemical sense.