I’ve been at this for a few days now 
and had a session with vagrant support as well. I’m going to add some logs and some of the errors I’m seeing here in the hope that someone will be able to help out!!
{ trellis } master » vagrant box list
netsensia/ubuntu-trusty64 (vmware_desktop, 0.1.0)
puppetlabs/ubuntu-14.04-64-nocm (vmware_desktop, 1.0.2)
{ trellis } master » vagrant plugin list
vagrant-hostsupdater (1.0.1)
vagrant-share (1.1.4, system)
vagrant-triggers (0.5.2)
vagrant-vmware-workstation (4.0.2)
{ trellis } master » vagrant -v
Vagrant 1.7.4
{ trellis } master » echo $PATH /C/Users/duncan/.babun/cygwin/home/roots/roots-example-project.com/trellis 1
/home/duncan/bin:/usr/local/bin:/home/duncan/.local/bin:/usr/local/bin:/usr/bin:/cygdrive/c/ProgramData/Oracle/Java/javapath:/cygdrive/c/ Program Files/Broadcom/Broadcom 802.11:/cygdrive/c/windows/system32:/cygdrive/c/windows:/cygdrive/c/windows/System32/Wbem:/cygdrive/c/win dows/System32/WindowsPowerShell/v1.0:/cygdrive/c/Program Files (x86)/ATI Technologies/ATI.ACE/Core-Static:/cygdrive/c/Program Files/Hewle tt-Packard/SimplePass:/cygdrive/c/Program Files (x86)/Skype/Phone:/cygdrive/c/Program Files (x86)/Bitvise SSH Client:/cygdrive/c/Program Files/Microsoft Network Monitor 3:/cygdrive/c/Program Files (x86)/MySQL/MySQL Fabric 1.5 & MySQL Utilities 1.5:/cygdrive/c/Program Files (x86)/MySQL/MySQL Fabric 1.5 & MySQL Utilities 1.5/Doctrine extensions for PHP:/cygdrive/c/HashiCorp/Vagrant/bin:/cygdrive/c/Program File s/nodejs:/cygdrive/c/Program Files (x86)/VMware/VMware VIX/vmrun.exe:/cygdrive/c/Program Files (x86)/Git/bin:/cygdrive/c/Program Files (x 86)/Git/cmd:/cygdrive/c/Users/duncan/cmder/vendor/msysgit/bin/git.exe:/cygdrive/c/Users/duncan/.babun:/cygdrive/c/Program Files (x86)/HMA ! Pro VPN/bin:/cygdrive/c/Users/duncan/AppData/Local/atom/bin:/cygdrive/c/Users/duncan/AppData/Roaming/npm