This question is two fold because somewhere in my attempts to solve the problem, I created a new one.

First:
I was trying to vagrant up using a Vagranfile based on the standard hashicorp/precise32 box. Everything worked up until default: SSH auth method: private key where it would eventually time out. Enabling gui in the Vagrantfile showed that the machine never actually logs in. I can use the standard user/pass and log in from that point but the vagrant up process still remains at that prior status.
Here's where my understanding might be a little dim. I've tried setting auth method from the insecure_pass_key to my root ~/.ssh/id_rsa or whichever one I wanted to use. I'm not entirely sure where to put a copy of the public key or my authorized keys file. I've got a .vagrant.d folder in my user dir (I'm on OSX) which seems to contain the box images. I've got a .vagrant folder in my directory with the Vagrantfile which seems to contain the specific machine I am building off of. I've tried pouring over the docs and forums but I seem to be missing a key concept here.

And Now:
After a host of tips/tricks such as rolling back by VirtualBox install, uninstalling/reinstalling Vagrant and VritualBox several times, when I try to run vagrant ssh-config with a Vagrantfile based on the same hashicorp/precise32 it says that the box is not enabled for SSH. Specifically, this error:

The provider for this Vagrant-managed machine is reporting that it
is not yet ready for SSH. Depending on your provider this can carry
different meanings. Make sure your machine is created and running and
try again. Additionally, check the output of `vagrant status` to verify
that the machine is in the state that you expect. If you continue to
get this error message, please view the documentation for the provider
you're using.

So now I am slightly up a creek. Any help would be appreciated if not just clarifying a concept.

Some pertinent info:

• I'm on OSX Maverics
• Due to the fact I'm running a dual HD system with system files on one HD and user files on another, my permissions are a little wonky and VBoxManage will only let me run commands via Sudo - not sure if it's pertinent - but maybe.
• I have no idea what I'm doing. That part is perhaps more important.