How do you setup a LAN (spanning multiple cable modems) over the internet?

[keyizm]

ultimately what i'd like to do is setup a LAN that my family & friends (Mac/PC in different parts of the same city) can join via a secure connection (maybe VPN or SSH). this would greatly facilitate file sharing & gaming. i know ... i know ... i should just setup a FTP server for file sharing and most recent games let you via TCP/IP but i've got some pretty computer illiterate family & friends and setting up a LAN that they could join would greatly simply things.
so ... any ideas? i'm pretty tech savvy, i just don't know how to go about getting all this setup. any ideas or suggestions would be GREATLY appreciated

[Pengu]

My guess would be with VPN...

[binaryDigit]

My experiences with VPN (PC only) leads me to opine that if the reason you are avoiding ftp is because of your friends/families lack of knowledge, then VPN is no better. It's conceptually simpler, but often times has problems that make it's use less than satisfactory. If nothing else, it's just much more complex to setup. There are gui based ftp clients available for both pc and mac that are very simple to use (some pc ftp packages even integrate into explorer (windows not internet) making for a pretty seamless experience).

Another alternative would be use HTTP since you can both upload and download files and you can provide a slick interface if you want to.

[keyizm]

pretty much all of my family & friends i'd setup to be on the VPN run WinXP so i'd use MS Remote Desktop and do the initial setup and create a batch script or have some client VPN program launch on login and they'd authenticate then. after that, i thought it'd be simpiler for them to be able to map drive(s), share files, and play network games over a virtual LAN (thanks to the VPN) vs. me getting countless calls and e-mails from the lot telling them what program they need to download and use. true i agree, the setup will be a royal pain in the A@# but after it's all said and done, i think the final product would be easier.