I went through this 2 years ago.
First, review your applications with NI Field Sales. They'll give you guidance on the Lookout package that best suits your needs.
NI sells a Modbus simulator that you can put on your desk and use to develop a virtual process with lots of objects. I found it very helpful.
Finally, going to Austin for a week and taking the formal Lookout Training Class was quite necessary, for me. I'm a Metallurgical Engineer by training, not an electronic or instrument person, so much of the jargon in the manuals was unfamiliar to me. While in Austin I received some necessary basic training, but also met several Applications Engineers that I still talk to occasionally when I need help.
Aaron Gesicki
Sparta, WI