although I never paid much attention to the "when" of it all, and simply picked it when I thought it was 'big enough,' I have heard that it is ready when the silks start to turn brown.

Sweet corn is ready when the silk has turned brown down to the tip of the ear.

Do you mean when it turns brown to the tip of the ear with the husk on or should I pull the husk back and and until it is brown to the kernels themselves?

I decided to pick an ear and try it out and this is what I saw. It looks like almost half the kernels aren't "filled up".
They look like partially deflated balloons. Does this mean I should wait longer, I waited too long, or does home grown corn just look like this.

Here is a link that might be useful: {{gwi:68730}}

I can't help you with the pictures but I harvested my first corn this year and mine didn't look like that. The first few ears, I picked early and the silk was brown down to the husk. When shucked, I noticed the kernals were not fully formed. They were not deflated as in your picture but they just weren't big enough to touch the kernels in the next row over. The next few ears I picked were still better, silk was brown inside the shuck, the kernels looked formed, touching the rows adjacent to them but the corn didn't have as sweet of flavor as I would have thought. The next few that I picked were just right! Nice big plump kernels, brown silk down into the husk, the juice was definately milky coming from the kernel, and just as sweet as could be. By that time, I had kind of gotten the hang of it and I had no more ears to pick. I'm not sure if this helps you or not but thought I would share.

What I usually do is wait for about 3 or 4 days after the silks have turned brown then I feel the husks. If they feel loose, then the kernels have not developed all the way. Just check them every day. I usually end up picking mine 5-7 days after the husks dry up.

Hmmm...that's strange. The only thing I can find close to that is perhaps you've experienced a day or two with a lack of water of any sort? Maybe it's 'starting' to dry up, but was fine before that?

So I should wait until the silk starts to turn brown inside the husk?

Check out 1st reply to this thread:

Here is a link that might be useful: How to tell if corn is ripe

I believe your corn is way past maturity, and has started to "dent" or dry on the cob. If the kernels are full of a mealy yellow paste, and are very firm and hard to crush, your corn is probably not edible now. (or at least won't be good) This being the case, about two weeks ago would have been prime eating time.

From that picture, your corn is at least 10 days to 2 weeks past picking time. nest year check your corn when about 20% of the stalks show silks. It will be ready in 21 days.