Higher energy π HOMO
from what I understand a higher pi HOMO is synonymous with more
  nucleophilic.


Yes, that's generally true.  If you have a substituent on a double bond that increases the electron density in the double bond, then the double bond (usually one carbon more than the other) becomes more nucleophilic and the energy of the HOMO and LUMO are raised.  Conversely, electron withdrawing groups attached to a double bond withdraw electron density, making the double bond less nucleophilic and lowering the energies of the HOMO and LUMO.

Comparing cyclohexanone enol (cyclohex-1-en-1-ol) to cyclohex-2-en-1-ol, you can draw a resonance structure for the former that increases electron density in the double bond (especially the $\beta$ carbon).  This electron donating resonance effect overwhelms the electron withdrawing inductive effect of the hydroxyl group.  Therefore, the double bond in the cyclohex-1-en-1-ol will be more nucleophilic and its HOMO and LUMO will be higher in energy than those for cyclohex-2-en-1-ol.