I can help with one question

The anal glands usually do NOT need to be expressed. If the dog eats kibble and their poo is nice and firm, that's all that is needed to keep the anal glands emptied

You'll know they're bothering them if you see them "scooting" their butts on the carpet, or they will STINK like rotting fish, P U!
I used to cut Starr's hair myself, but now that she's gone, I just havent' had the heart to do Luna's and Izzy's. So I take them to the groomer. I absolutely cannot cut their nails myself, the first time I tried with Starr, I cut it way too deep (she moved at the last second

!) and it took me a few hours to get it to stop bleeding. I threw away the clippers right then and swore I'd never ever touch another pair of them. It still makes me nauseous to think about it, but that's just me