I use ohmyzsh for my local shell and one feature that really spoils me is the ability to tab complete without matching the case.
By default, Ubuntu and Homestead do not have this but support can be easily added by running the following command inside your VM:
echo set completion-ignore-case on | sudo tee -a /etc/inputrc
Next, exit the VM and ssh back in. Your tab completion should now be case insensitive.
Hat tip to Matt Stenson for this.