True, it's all about timing and just asking. Did this at a roadside hotel on a long drive once, saw the empty lot and walked in. Told the guy at the counter I needed a place to crash and asked for his best cash rate. He shrugged and gave me a room for forty bucks flat, no tax or anything. The booking site price was almost double. Feels like a lost art now for sure.
Wow, this actually hits different after the pandemic. I used to totally agree that the skill was dead, but during lockdowns I saw empty hotels and just called one directly to ask about a last minute rate. They were so happy to have a guest they knocked off like 30%. Made me realize the sites killed the habit, not the chance. Sometimes it still works if a place is clearly desperate.
Have you ever tried this with a big chain hotel? I called one when their app said they were full, but the front desk guy told me his system wouldn't let him override the rate. It's like the corporate rules tie their hands, so only smaller spots might deal. Makes you pick your battles, right?