> Do you use it even if you plan the trip well in advance?
Yes, often. I'll check there first at least.
If it's a special occasion (Valentine's Day for example) I'll probably use another booking platform.
> Have you ever run into problems finding a room or being forced to take a room in a distant part of town?
Yes, never been worse than the main booking sites though. I was in SF at the same time as the Salesforce conference was taking place a few years back, for example. Nothing available anywhere.