In order to properly judge the fit of your trousers, you'll need to take a couple pictures with a proper shoe on.
As for the jacket, it seems that you're having some issues with the upper back, namely the collar roll. It's not stemming from the point to point being too small (in fact, it's interestingly a little large), but rather from your traps pulling on the garment. Also, with your sloping shoulders, a jacket with a little softer roping might get rid of some of the dimpling you're seeing. Either that, or reducing the width of the shoulders and/or halfback. When it comes to the flare that you're referring to, by letting out the waist of the jacket a little, you'll help it drape better. Yes, you're in shape, but you don't need things to be painted on.
The vest fits wonderfully.
Overall, it's not bad at all, and I hope you enjoy wearing it!