There is a renewed interest in boot cuts, flares and 70s inspired in general. So I think the pants in #4 work. However, I would wear them with much shorter shoes so the hem is just 1/4" above the ground. They would look cute with a Boho type of outfit. For example, a flowing peasant type of tunic and sandals. Or, go 70s glam by pairing them with a luxurious wrap sweater or wrap jacket. The other idea is to wear them with a big sweater and cute sneakers.
As for the length of the first pair, I have a hard time saying unless I see the pants from the front. To give me an idea, I collected some pictures of contemporary trousers. I think the first ones from Alice & Olivia have been Angie picks. The second ones are shorter which is how a lot of pants are now. The third pair have the slouch factor. It really depends on the kind of look you're going for.
The kinds of shoes you wear with them depends on the occasion. If work, you could go for pumps. Oxfords work too, and if that's what you want, it will influence the length.
I don't think the jacket is too tight, but the sleeves look too long. Do you feel it reflects your current style or do you want to keep it for sentimental reasons?
By the way you are in amazingly good shape, your figure looks like a teenager's not a new mother's.