I'm all windows 10 so did my first print with RepG and also tried MakerWare but quickly made the switch to Simplify3D and did't look back. BTW Simplify3D works with Macs.
Just finished adding a glass build plate so will see how that works. Some of my first builds where Filament guides and filament spool adapters. Which helped prevent filament tangles.
I was looking at the Astrobox site last night and was thinking about building one. So I would definitely be interested in your Astrobox experience.