As others have already mentioned taking the essential course will get you the basics in simpl and VT-Pro to be able to program a basic system (the only crappy part is that I believe you have to take the intro to Crestron and SB classes prior to the essentials class now).
One thing that I haven't seen mentioned is using tech support is key. They are there not only for the hardware side but also the software side and I haven't had a bad outcome when on the phone with them when I am programming. They are
As someone else stated reverse engineering the Crestron sample programs is the best way to learn to program in Simpl. There will likely be a lot of symbols that you haven't seen before or understand but all the basic programming will be there.
The more time you have to sit down and work through the programming the easier it becomes and more proficient you will be with it. For basic systems (once you get good at them) you will have them programmed in a matter of a couple hours as I am sure majority of the products you are using will be the same, and for the products that aren't the same it is just a matter of changing a User device rather than having to alter programming, essentially building a template to program from.