Yeah definitely having another server in the other office is the way to go, adding it as a global catelog server and an Active Directory replica will allow the remote PC's to authenticate locally rather than over the VPN (if you didn't have a VPN they wouldn't authenticate at all since all).
Which also shows why using a VPN is an advantage, in the event that the local server is down or can't authenticate the users the traffic can then go across the VPN and authentication can be done on the 08 server.
8mb/1mb is good connection most of our clients run either 2mb/2mb or 4mb/4mb (premium SHDSL) and they don't have any issues (mind you we have GPO's and firewall rules to stop certain browsing/streaming.
In some of our sites we have also put a separate connection in but that's for VOIP purposes only.
Off the top of my head I'm not too sure what you can do about the attachments; how big are they? Are there always going to be emails this size or is it just during the transition?
If it's just for the transition just setup one POP connector and then increase the size limit to see what happens, if that goes ok then I'd try another one or two.
If it's going to be all the time I'd try and keep most email to the 5mb limit at most, or schedule to send email over that size after hours (which can be a pain since people want email NOW not later, so you'll most likely have people complain).
Another option is DFS and FTP depending on what you want to achieve. If users what to be able to access files in both locations you should use DFS, but if it's that they just want to send people large files you'd be better off setting up and FTP site
(Preferabley on a separate box doesn't need to be a server an XP workstation will do the trick but remember that there is a total maximum number of 10 connections to a FTP server that is hosted on a XP workstation at the onetime)
I'd definitely keep the VPN for the simple fact that all company data will be encrypted including Active Directory replication, DFS file system (which will be intergrated into the AD replication if you set it up) along with another information.
Basically I think you should sit down and work out exactly what users needs are and then decide on what option to take, there are so many different ways to go about setting up WAN's but it all comes down to what the user's needs are.
Let me know how you get on with the POP connector, I'll give it better thought and get back to you if I have any better idea's.
Personally my preference for this setup would be something like setting the second server as an Active Directory replica/global catelog, configuring the VPN to pass the replica traffic and another company data.
Depending on what the client's needs are I'd be inclined to setup either FTP or DFS and show users how to send large files rather than through email.
Also I still think Outlook is the way to go for users Email, it's much easier and covenant for them to simply open Outlook and there is their email rather than open their browser log into and read/send email.
Oh yeah backup's have you considered how and what you will use to backup, also what you are going to backup?
With the remote site if you do use Outlook, get the users .pst files and move them accross to the local server so they get backed up with your nightly server backup (if that's how you do your backups).
You don't want to have a PC fail and then need to post or worse yet get the user to pull down their mailbox to their new machine or profile.