It does look tight in this picture. His hair is super duper thick (he's a curly horse) and it makes it appear tight. I always make sure that I can fit my fingers in some.
I think it looks too far forward also. This is the problem I've posted about the "cinch placement" before. If I put it farther back, then the cinch is no where near his "armpit". Do you think that for this type of saddle, it's ok to have the cinch placed further back? I've only used typical western saddles and this one has been a bit tricky for me to figure out.
I'm not an endurance rider, but Newby, I think I used to have the exact same saddle. (Mine was a Bighorn.)
Anyway, the cinch on this saddle should NOT be in the armpit. That is fine for full-rigged, normal western saddles, but the rigging on an endurance saddle is supposed to put the cinch farther back to avoid galling. In other words, by design the cinch should be farther back, so that if you did a long endurance ride it would not rub the horse under the arm.
What I would do is sit the saddle on the horse a little forward and then slide it back until it hits the sweet spot behind the shoulder. That area behind the withers (which is hollow on a thinner horse) should be where the saddle tree naturally lays. Slide it into that position (hopefully you can feel it slide into the right spot) and then cinch up with the cinch hanging straight down from that position. It will be farther back because it is designed to be.
I'm not much help with how many times the strap goes around the front ring, etc. I don't remember and even if I did, I'm not sure I ever had it right either.
For simplicities sake, you can even ignore that back ring and only use the front. If you are only pleasure riding, that would be fine as many people don't ride with a back cinch. And that would actually allow your cinch to be farther forward as well.
It will take some experimentation to find out what works for you and your horse. I have found that with some horses (chubby ones like mine) that if you try to use the cinch ring farther back it will start creeping up under the arm pit and taking the saddle forward as it goes. Then the tree will be riding up on the shoulders, which is not what you want (actually, it would look exactly like your picture). But don't worry about that at the moment. Slide the saddle back into the sweet spot, cinch the horse up with the cinch hanging in whatever position it wants to be in, and don't try to force it under the armpit, and see how it goes.
You can try it with the endurance type rigging that a photo was posted of, or just for normal riding, just use that front cinch ring and ignore the back one. That might work even better for you.