@David:
It's possible to get issue one resolved so it works properly in version 2 beta right now. If you go to System->Routing, add a gateway on the LAN Interface with a Gateway and Monitor IP of the LAN IP address of pfSense. Then, go to the Routes tab, and add a new route where the Destination network is the subnet of the remote network that you are trying to access pfSense from over IPsec, and the Gateway is the LAN gateway you just created. Once you save this, you should be able to access services on pfSense itself from over the IPsec tunnel, assuming firewall rules on the IPsec interface allow it. I have this working myself. It's a slight modification of the steps given at the link you provided to the Wiki with the description of the problem, since the UI changed a bit in pfSense 2.
David,
I can access the resources just fine from the remote PFSense router (or at least as well as I want to), the issue lies with Apple Remote Desktop and not being able to remotely administer machines. With a PFSense->SG300 IPSec tunnel I can administer them just fine, with a PFSense->PFSense tunnel I cannot. I did get an OpenVPN tunnel setup at one point and that works well, but that doesn't work with some of our clients' firewalls.