Higher energy π HOMO

Which is higher in energy? Cyclohexanone enol or cyclohex-2-en-1-ol?

Okay from what I understand a higher pi HOMO is synonymous with more nucleophilic. So I would expect cyclohex-2-en-1-ol to have the higher pi HOMO because in the case of cyclohexanol enol there would be inductive withdrawal by the oxygen connected to one of the sp2 carbons involved in the pi bond.

Or would it be the other way around? Resonance donation by oxygen into the pi bond of the enol makes it more nucleophilic? How can we tell how the HOMO/LUMO energies split?

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.