MO was our go-to for our annual winter getaway stint for the last 4-5 years. We'd never been upgraded even through our Virtuoso or MO Fan Club bookings. We typically booked the legacy CityScape Suite (City View 1 bdrm) or StripView Suite (Panorama Strip View 1bdrm). I think this was in line with most people saying MO was pretty stingy with upgrades.
Fast forward to this weekend, I'm not sure if it was because of Hilton Diamond status, room not being ready after I arrived, or having the HHonors Aspire card, but we were able to get an upgrade to the legacy Dynasty Suite (Villa 1 Bedroom Suite) from night 2 of our 4 night stay. I booked with the promotional rate of stay 3, get 1 night free. And with the Wrangler National Finals Rodeo in town, I wasn't too hopeful, but am happy things really worked out in our favor.
So far, I can't really tell a huge difference from MO so both my wife and I are very happy. With Diamond status, the $50 daily credit apparently applies to all food/beverage, and with the check-in mishap, we effectively have $250 in food credit, so not that much different from MO Fan Club.