Best Way to Make Line Art From Scratch

Question

Hi and I apologize if a basic question, but I've created a rather complex illustration, and I'm wondering if there's  a quicker way to go from y first attached image, to the transparent second. I feel as if I'm spending a lot of monotonous time following a pattern of Minus Front, and Make Compound Path to set the black background up for another round of cutouts. All black in the image is one filled shape encompassing the entire back of the drawing, while everything white is white fill blocking out the black space, or other white objects below.
How can I clean up my act? Or what would be a better strategy from the beginning to achieve transparent line art?
Sincerely thank you for your replies, I'm wasting far too much time here, I know it. Happy to clarify any left out details!

Answer 1

Your basic problem is you are not working methodically and planning as you go. You are drawing a large number of paths willy-nilly until the whole drawing is "done" merely in terms of how it looks on the screen and figuring you'll just deal with the inevitiable decisions of how it is technically organized later. Then you discover you've created an unwieldy and confusing number of objects which you hope to resolve into understandable (therefore predictable) simpler constructs as a last step.
It's far better to have in mind what kind of constructs and general organization you want to end up with and work toward that, completely finishing (trimming, unioning, etc.) each elaborate section accordingly as you go. That way you avoid confusing yourself and creating additional work later when you think you are finished with the line work and want to draw the fills. As you work, always keep in mind what kind of objects you are creating: Each path is either open or closed, filled or unfilled, stroked or unstroked, simple or compound.
Drawings like this may be organized several different ways. None is "right" or "wrong"; but you just create time-wasting frustration when you fail to plan for it:
All line art completely trimmed, without resorting to fills in one area to "hide" unwanted portions of the line work in another area. A separate stack of unstroked filled objects behind the line work to create the coloring. (This method can greatly simplify the issue of trapping.) Some users even prefer to create all the fills on one or more separate Layers (although it's not necessary to do so).
Line art drawn more willy-nilly, with the intention of resorting to LivePaint to do the trimming, filling afterward. Some users live and die by this method. I don't, because all such automated routines invariably create what would otherwise be unnecessary additional anchorPoints, and resulting fills merely "kiss" their adjacent line work, rather than underlay them. That can necessitate more elaborate trapping.
Line work and fills shared by the same paths. Sections of the artwork treated as separate Groups (helmet group, visor group, etc.) An advantage of working this way is that the resulting overlaps allow the relative positions of the pieces to be tweaked later.
Again, it's not that one organizational method is right or wrong; the point is that, like it or not, vector-based drawing is all about creating a stack of independent objects. That is fundamentally different from "painting" in a raster imaging program. By its very nature it imposes a need for intelligent organization of that stack. So you're far better off always at least generally planning for that unavoidable organization, regardless of which scheme you choose. The reckless abandon approach to drawing is antithetical to the nature of vector-based drawing.
For example, consider the leaf designs on the visor. As you've drawn them (evident in your second and third screenshot), they spread into an adjacent area where you intend them to be partially hidden by a white fill in front of them. There's nothing strictly "wrong" with working that way (although I consider it untidy) but it suggests you intend to build your drawing according to the third organizational scheme described above. But that conflicts with your trying to correctly resolve your line work by means of automated routines (outlining strokes, Boolean path operations) later whidh is more appropriate for the first organizational method described above. So using those automated features will in some places cause the unwanted portions to re-appear as the object stack changes (as you can see occurred in your third screenshot). So now you've got stuff that needs to be trimmed away. You've created additional work for yourself.
From where you are, based on your first screenshot, you could try this:
Select All
Object>Path>Outline Strokes
Select All
Pathfinder palette: Merge (unions touching fills of same color and punches overlapping objects of different color in one move)
Do the necessary trimming and correction of unwanted stuff that was previously hidden.
Do any necessary corrections of path direction or winding rule, or compounding to flip fills to voids or vice-versa.
Either create your fill objects behind the line work, or use Live Trace to create them.
Because of the runaway number of paths you have drawn, you may have difficulty doing the above set of steps. If so, try working it in several "sections"; for example, with the black pointer marquee select across half or a third of the drawing, do the steps, then repeat for the next third, and so on.
And don't worry...after you've done this kind of tedious after-the-fact cleanup on a few projects, you'll start to understand the principles of pre-planning the organizational structure of your drawings and start keeping that in mind as you proceed. We've all been there.
JET