From my own experience it does seem to depend on where you were at calorie-wise when you started. So many people use 'maintenance’ calories as a starting point and either add or subtract from there to either gain or loose. The problem I have found with that is the maintenance level for myself changes as I increase or decrease calories.
For example, a few months ago I determined my maintenance calories at about 2500-2600 cals/day. After a couple weeks at this level I neither gained or lost. Then I started to bulk and went to 3000 cal/day. This worked great for about 2 weeks, then my gains dried up. I then increased my calories to 3500 cals/day and once again started to see gains for a few weeks. The gains have stopped once agian and I've been stuck at my current body weight for about three weeks now.
It looks like my 'new' maintenance level is 3500 cals/day as I am neither gaining or loosing. If I want to continue to bulk I'm going to have to increase it to at least 4000 cals/day (there is now way I can do that 'clean'). Is it possible that your body adapts to an increase (or decrease) in calories? Maybe that's why we hit plateaus when cutting. Most advice that I've read is never go below 2000 cals/day when cutting. If I had started cutting when my maintenance level was at 2500 cals/day then I would only have 500 cals to play with. If I were to start cutting now, I would have 1500 to play with.
Anyway those are just my thoughts, I'm sure Bobo and others would have a much better explaination for this.