A plea for help

The raging headache I’m experiencing could be a result of my social conversion therapy or perhaps it’s a result of the design assignment I’m currently working on.

I’m trying to make a vintage postcard.  I’ve been following this tutorial on Youtube, and it’s been helpful for the most part:

I’m having zero luck filling “the village” with the rover image you see in the video below.

So far I’ve tried the method described in the handy tutorial and my video above (selection to alpha > shrink (optional, I think) > invert > cut.

I also tried these easy steps and come out with this:

Screen Shot 2015-07-24 at 6.01.31 PMThe outline of the font has the rover image, but not the inside of the font.  What am I missing?

Hmmm…  Maybe it’s a poor font choice as I just followed the easy steps and came out with this:

Screen Shot 2015-07-24 at 6.05.38 PMOK…. Maybe I answered my own question and need to go on another font hunt.  So….