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I am an extreme novice so bare with me. I'm attempting to prepare a logo for water jet/ plasma cutting and need the negative space in my text to have a bridge to the base material. I've watched a couple tutorials but can't seem to successfully accomplish anything. The attached pictures will show the use of the rectangle tool, followed by selecting the letter with the Pathfinder, and selecting "trim". I will get an error every time stating that I need to select intersecting paths. I thought it might be due to the text being in outline but when I try to fill the text, the negative space is filled as well (another issue?). I'm currently working on the file in DXF format but I tried in eps also. Is the art or initial file just corrupt? I'm assuming that I am just approaching incorrectly.
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In that particular scenario, try Minus Front, not Trim. Trim removes overlaps from below filled shapes.
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Create a compound path (Ctrl+8) from the 'A' first.
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Without changing anything the A worked and the O by using minus front. I'm now back to nothing working on any letter. I attempted "ctrl-8" on B but then the internal holes disappeared rather than the rectangle
 
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It's difficult to advise further without seeing the file. Try shape builder tool (Shift+M). Select the objects you want to work on, hold alt and click on the areas you want to remove.
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I would gladly email it. I know it's a big ask, but if you feel like taking a peek it's greatly appreciated