Hey Nate,
Thanks for the great feedback. I am also a fan of the SketchUp's simple and efficient tools. If you look over the past 5 years (maybe even longer) the TBC team has made great improvements on the CAD front - snaps, drafting module, and many more. I think you will see more improvements as the software grows.
CreateCOGO was developed to be an efficient way to create lines and points using distances, bearings, etc. I find it one of the better methods for key-in of parcel lines and construction plan data, especially on a grid! The video tutorial below:
TBC 3.80 Create COGO - YouTube
There are some great tutorials on using the Drafting and CAD tools in TBC. If you haven't had a chance before, check them out at the link below.
Trimble Business Center: Tutorials | Trimble Geospatial
Happy surveying,
Riley