I'm not a coder, so I'm not going to pretend that this solution is easy to implement (it might be, but I wouldn't assume so), but how about allowing you to expose the "expert" options just temporarily (to find the tool you need) and then allow adding that to your new "novice plus" custom menus? I.e., if you use a menu option from the expert menu X number of times, it just shows up even though your default is the novice view.
It seemed that way to me but I have done enough work with computers (I am on HN, after all) to know that things people in general think should be easy often are not, and things they think are hard may be simple. Thanks.