We moved DS1 straight from the cot to a single bed, so that DS2 could have the cot and DS1 just have one transition. It worked really well. We started by reading the bedtime story on his "big boy bed", then asking him where he wanted to sleep. THe first two nights he pointed to the cot. The third night he stayed in his new bed. And we never had any problems. Recently we converted the cot into a bed for DS2 and it took about 2 weeks to get him to sleep in there without climbing out all the time. I think this is more a personality thing than anything though. Trust your instinct and do whatever you think will work best. And GL!