My sad story, herein.
Bigwig client: not too computer savvy but brokers multimillion-dollar real estate deals, fortunately good-natured.
Me: fairly savvy but no six-figure commissions.

The server: Bone-stock SME 6.01-01.
The VPN client: Dell Latitude laptop XP SP2.
The laptop was running Windows 2000 and had never left the office; bigwig heard that I'd set up a remote access solution (which I use almost daily, from a Win2K machine behind a SME 5.6u6 server). Bigwig wants to take his laptop on a trip & connect to his Exchange server. So I take the laptop, upgrade it to XP SP2 (probably my big mistake, but it's so much nicer for wireless connections & security) and test the PPtP VPN successfully about a gazillion times. (Okay, not a gazillion really but at least half a dozen successful attempts and NO failures.)
He's leaving town today, so we walk across the street to another client's office for me to show him how to use his new capability. I'm feeling pretty good about this and confidently fire up the desktop icon.
"Verifying username and password" ... for far, far too long. Then the axe descends in the form of the dreaded 619 error.
I'm red-faced & stammering, as I've successfully connected several times with this laptop, and Outlook was perfectly happy talking with the Exchange server (hint: entry in HOSTS file). He goes away after poking some fairly good-natured fun at me; I slink away to my office figuring there's something funky about Office #2's setup that's interfering.
In my office, using the EXACT SAME setup under which the laptop connected several times without fail, it won't connect even ONCE. My 2K workstation, on the same network (though it has a static IP, for what that's worth), connects about 1 out of 3 tries.
Nothing I try works, including rebooting the SME Server and the recent KB884020 VPN issue fix from Microsoft. Time's ticking but I figure what the heck, I have skills, let's see if OpenVPN will do the trick. I look up the HOWTO, roll up my sleeves & get started. Oops, the bigwig's office network JUST HAPPENS to use 192.168.100.X for its IP range, just what the OpenVPN expects for the traveling side. No problem, think I, I'll just adjust all the parameters that formerly read 192.168.100.X to 192.168.111.X and all that read 192.168.1.X to 192.168.100.X.
Service OpenVPN Start: [FAILED]
So there you have it. I'm technically humiliated and out of time and the bigwig is in the air, laptop-less. C'est la vie.