> 1. Does SBS remote access need to be configured to allow
> a user in a foreign country access?
AFAIK, No. The internet is one big country :-)
> 2. If so, was his dial-in experience most likely due to
> dialing up a US phone number (again, not sure what he did
> dial)?
Most probably because he used a different ISP.
> 3. If 1 and 2 are 'no', what should I try?
Call the high-speed ISP or change to another one. See below.
> 4. Could it be that his ISP doesn't allow VPN
> connections?
Can he check if there is connectivity between the laptop an the server? A
simple ping/traceroute to whatever.yourdomain.com should work here.
One possibility is his ISP in Costa Rica is blocking protocol GRE47 (PTPP
passthough) somehow (or maybe TCP 1723). I think there is a way to test
this... if I find a link I will post it. However, it is unlikely that he is
not getting an error message back... at some point the VPN connectiod is
going to say something. I would make sure that he is telling you the truth
about the error :-)

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Javier [SBS MVP]
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