A hundred beans a project is pretty light for an experienced Pronto programmer, especially if you need to do the travelling to the site on your own dime, and with no benefits or other $$ analogs.

With no experience with the higher end systems, you will find it pretty hard to get started in any regard. Programming those things, as I expect you know from your Pronto experience, is as much installation as it is programming. Once you've sat down to begin, without having a class to help you start, you are looking at days or weeks, I promise you. At $100 per job, the carrot is pretty small (and shrivelled!), and that stick is mightly long.

A flat rate is not the correct way to bill for this work. It does not take into account anything such as the complexity of the system, access to the site (Elmhurst project you can walk to vs. Water Tower Place job you need to drive to, park, clear security, wait for elevator, etc.)

I believe I can program a single room Crestron system top to bottom and test it, using one of my templates that I know by heart, in under four hours. A flat rate of $100 is not enough to get my heart racing, I can tell you.