What I would do is the following:
Ask the IP space owner (person allocated to) to send an e-mail to
Brian,
requesting the block to be advertised over BGP (needs to be /24+,
or collection of networks /24+) and Cc me in this e-mail. I reply with
the ASN, route objects that need to be created, etc. Brian hopefully
approves the request.
Afterwards, I advertise the /24 via BGP to the Internet.
Then, I arrange with the IP space owner how the space will be router
to them. I
can support OpenVPN, PPTP, L2TP, GRE, IPSec, etc.
I think he means "after I connect to a VPN server in the USA or e.g. in
Greece, how do I make it send the traffic for my Israelian subnet to me
over that connection".
That is by far not that complicated.
He only needs to connect to that VPN server, he will get an IP from the
address space of that server, and setup BGP over that connection (using
an agreed-upon private AS number) and announce his own Israelian subnet.
The BGP protocol will then exchange this information with all other
interconnected VPN servers and they will all route his subnet to the VPN
server he is connected to, and that will route it to him.
Traffic from internet will still be routed to UCSD as part of the
default network announcement, and the router there will first route it
to the VPN server he is connected to, then to him. No need to announce
his /24 on internet explicitly!
Of course this gets more difficult when the IPIP mesh is kept in place
and is used as backbone.
Then the VPN gateway he connects to needs to add his subnet to its list
of handled subnets, via the portal.
This means he can connect only to a single VPN server and have working
routing.
When that server goes down, he would have to arrange that the portal
information is changed, the subnet being removed from that gateway and
added to another.
Without IPIP, he could simply connect to two or more VPN servers at the
same time, and as long as one of them is working he has connectivity to
everywhere.
Rob