Here's an update for anyone else that tries to do this the way I did it...
Basically, if you're going to do this, I'd recommend you don't dremel or feather out the edges like I did, and instead lightly sand out the gouges to flatten the surface a bit to get better surface area and leave it at that.
After sanding I used a poly filler (White (a little gray) Evercoat Formula 27 - dried in about 20 min and sands down easily). I wet sanded the filler with 400 and 600 grit and left it slightly higher than the gouge (because I was trying to cover the mysterious blue paint below the white). Then I applied the white gel goat (mine was in a kit so I mixed in white coloring to a semi-transparent poly paste). Then I wet sanded that down to even things out but still keep it a little thicker over the poly paste because it was still showing through a little bit.
Attached are how it looks now. Worse than when I started, but my standards have fallen since then. The close up you can barely tell (yes there are a couple craters in the gel coat but since I'm leaving other gouges that stick out more, I'm not too worried about it at this point. The zoomed out version you can tell the area is darker, probably just poor color matching on my part (like everyone says, it's nearly impossible to match, and adding the hardener darkens it so it is even harder to match). I'm hoping that once I compound, polish and wax this won't stand out as much (because the hull will look "wetter"?), but perhaps it will stand out more.
Overall the money and time (days) I spent trying to fix these dings was mostly ineffective (arguably counter-productive) but a great lesson non the less!
At least I wasn't messing up someone else's boat...
In other news I have a new gas tank installed and the engine runs great. Will be on the water before you know it!