Yes, I've seen Dewitt Jones's prints in the local galleries, and I knew that he lived there, but haven't had a chance to meet him yet.
If you go in the winter, pay close attention to the weather. Last December we were out there during the storms, and the airport got shut down for a few days, and roads were periodically impassable due to mudslides and flooding on the east end of the island. If you're planning to stay at a condo during the winter, I'd recommend staying on the west end of the island toward Papohaku beach or close to town, at someplace like the Hotel Moloka'i or Moloka'i Shores.
We may go again this winter.