Trying to create a 3D print of a spray paint stencil and I'm having difficulty joining 'islands'. What I'm doing wrong? I'm trying to create a spray paint stencil in blender and then 3D print it so I can use it for spray painting. I'm having difficulties joining the 'islands' to the rest of the stencil. For example, in the following screenshot, I'm trying to join the hole in 'd' and 'o' with the rest of the stencil
 

What I have done is the following:


Create a text object, change its font, text, etc.
convert text to a mesh (Alt-C).
create another object (I've tried planes and cubes) which I'll refer to as the 'stencil', and make it 10cm x 4cm x 3mm 
Apply a solidify modifier of 1mm to 2mm
Apply a difference Boolean modifier on the stencil with the text mesh


What I attempted afterwards was to go to wireframe mode and join the faces together, but I had to subdivide several of the faces.  What happened afterwards was that I keep getting manifold edge errors from the faces I created and when I attempted to dissolve the edges, it ended up deleting a vast majority of the stencil's face.

I've also tried doing a bridge edge loops, but because of the curve natures, what I ended up with is this mess and 28 bad contig edges error.



Clearly whatever I have in mind isn't working out too well. Does anybody have an idea on how to make this work?
I think the normals on the inside of your main character profiles are flipped .. it would explain the twisting on the bridge. Also remember, to be tidy, Bridge Edge Loops needs an equal number of vertices on both sides.

Try a quick CtrlN 'Make Normals Consistent' on the entire mesh in edit mode.

Have a look to see: in Edit Mode, Properties Region > Mesh Display panel > Normals > Face..

It would probably be easier to create the bridges in the flat, before extruding the thickness of the piece.. you could, instead of using a Boolean, Knife-Project the text down on to a plane, make the bridges, and then extrude.