I was thinking something along these lines.
It won't sound like you are disagreeing with the friend if you point out the mare's big belly. Then you add in a normal voice that she might need worming.
When I was working outside in cold weather I would wear two jumpers rather than a coat. I was warm and cosy and could move easily. Coats can be restrictive in comparison.
I've had two horses, both mares, who I feel had the wrong temperament for me. I like a sooky, please-look-after-me horse, but these two were independent types. I'm not saying the sooky ones I've owned have done everything I asked willingly and with good manners. No. Sometimes they didn't want...
It almost sound like you like black so much because of Jet. But he is also a cob, a nice height, sensible. So maybe you really like him for those last 3 traits.
I think the reason the terrier is chomping on your trouser leg is because there is no making sense of how a treeless saddle can do what a tree'd/treeed saddle is meant to do.
Tell the terrier he can rest now. He might be exhausted.
I've heard from a good authority (local long distance runner, well known in these parts) not to run down hill because it's terrible for the knees. Just run in all the other spots. (He advised us not to run up hills, but only because we would conk out and give up entirely. Running up slopes or...
I don't think anyone doubts that he has a lovely varied workload. He sounds like a lucky horse. He's just stating that he'd like to be out there where the good stuff is and, er... [starts the bend] maybe we should just...
It's no big deal. Just ask for what you want before he starts.
:)
Oh, and another thing, you know when the issue will crop up, so start your aids a little sooner. Pip him at the post, so-to-speak.
He's not going to 'learn his lesson'. I think that's the wrong mindset. You have to be ready and prevent him from doing it.
Just my thoughts.