since I work for a company that estate sales, I can tell you..as part of your estate planning, if you think your family will not know what to do...get with a company now and start going over what will need to be done!
Also go through your stuff...start passing on things NOW...that way you will have a FEEL for who really cares and who could not care less....find a local charity and start working with them to see if really want/need your stuff later on....
OR get off the computer and start using that stuff up..hehehe