I am almost completely paperless as well. You can get free converters and print just about anything to a PDF (ex:
PrimoPDF), then file it electronically. Plus I scan some of the paper stuff so I can file it on the computer as well.
For client related stuff, I could never figure out whether it was better to file by subject or by client. But have finally decided that by client works better for me.
I have some suggestions for electronic filing. I recommend that you set up a filenaming standard that you stick to so it is easier to find things. Like maybe including client name, subject, date (ex: Smith-Contract-090324.doc). Then if you are filing by client, you can also do an overall file search for all your contracts when you need to see all of those. Or vice-versa.
You could leave off the client name if you are using a client folder, but I find it helps to have it there in searches. If you do a search for all your contracts, the client names will be there to help you.
For the things I want to sort by date, I put that at the beginning of my filename and use yymmdd because that sorts properly.
Deb