At the moment we're stuck with the dreadful PPTP connection.
We've been using HOSTS file for over 4 yrs now. I'm tired of it and my first
task when I joined was installing a DNS server. It's been running fine but
the binding order isn't correct. Then again, the domain we use both servers our
internal and external use. When I VPN into corporate, I can't resolve our internal
servers. Our domain is registered through register.com (f'n hate them) and they also
serve our DNS info.

Silly question but I created an A record on register.com that points one of our internal server to 192.168.10.100 which points to the internal IP of the server. Please note, the server is not accessible from outside. Is it a good idea to do this? I dont want someone just pinging things randomly and seeing our internal IPs.

Nobody outside of your company will be able to reach your server by connecting to 192.168.10.100, because the IP range 192.168.0.0/16 is not publicly routable. If they're lucky, they'll reach some computer in their own office. Or the box in their living room, if they have their router set up in a particular way.

Still, I don't think it's a good idea to have private IPs in public DNS registries. It just doesn't make sense having that information hanging there for all to see.

Yes, I realize no one will be able to connect to our internal, but I'm referring to those using VPN. Once I connect to the VPN, their laptops uses their LAN's DNS to resolve the domains. I was able to "fix" this by creating A records on register.com and give them our internal IPs.

I agree, I dont want our internal IPs listed publicly.