If you go the dynamesh route then you'll probably want to close the holes or restore the deleted faces before using it. Dynamesh prefers the model to be 'water tight', otherwise the results can be more unexpected.
Thank you! @cryrid and @musashidan Turning off Smt (subdivide smooth modifier) worked like a charm! Also, Dynameshing the model was the better rout for this particular project, thanks for the info!
Somewhere along the line in the last few releases the creasing on open borders got broken and doesn't work as expected. Disabling the Smooth modifier as @cryrid suggested will work. However, using dynamesh for this would be much better. It will give you optimal sculpting topology. The topology on your basemesh is…