I also don't have as much devices as you do but I still thought the whole process of migrating from ST to HE was going to be hard. I took someone's advice and did it room by room. Basically moving stuff that was too integrated with other stuff in the house. I also moved Webcore Pistons as I went but soon realized that my HE hub was crawling. I started to look at RM but I couldn't wrap my head around how it worked. However, I knew that I had to move away from WC if I wanted success. I started with little rules in RM and really started to get the hang of how it works. Really easy, just don't over think it with RM. I just have two WC pistons that I need to keep right now and I still have my iphone's as presence sensors in ST which I use Hub Link to pass the presence to HE. Like other users, the big difference is the speed at which things happen. The lights go on instantly when motion is detected. With ST, I would be down the stairs and in the room(in the dark) before the lights would turn on. So frustrating!