Hi Shellie,
First let me say that I appreciate very much that you are getting involved with this post. Too many companies don't care about what their customers have to say when it comes to negative criticism.
If it's possible to use Dealersocket on a mac without any issues, I'm all ears. What browser is your CEO/CTO using? I've used Safari, Firefox, Chrome, and even the antiquated IE for mac and none of them function properly. The typical culprits are buttons such as for marking status for uncontacted, demo, write up, etc, or for sending emails. If I can use it on my mac without using vmware fusion and windows 7, I am a happy camper.
As far as the email situation goes, this is the issue: When a brand new lead comes in, I can reply and it logs that email and sends it to the customer if I reply. However, if the customer is just responding to one of my messages, responding to that message does nothing. It doesn't show up in Dealersocket and the customer doesn't get the email. I've checked with them and they did not get my email when I used this method.