I've been enjoying these updates Kubby. In regards to bread, are you choosing white bread or wholemeal? I think wholemeal tends to have more vegan choices but you still have to read the ingredients. I just did a quick search for US brands and found this: https://www.livestrong.com/article/185769-which-brands-of-bread-are-vegan/
Also, local bakeries tend to be more vegan friendly as their bread has a shorter shelf life than supermarket breads, so there's less 'other stuff' in them.
This might help you too: https://www.peta.org/living/food/accidentally-vegan/ (check labels though in case they've changed)
When eating out, I always specificy "no dairy/cheese/eggs/mayo" etc. dependingo on what it is I'm ordering. You can always say you are lactose intolerant. That makes them a bit more honest, cos you could sue them (God Bless America!).
In the US you can also ask for the allergen list as well as many chains have one. Then you can easily determine what's vegan or not. Also, check the websites of any might go to regularly. Here's a couple I know about from youtube.
http://www.subway.com/en-us/menunutrition/menu/~/media/9C781D304C254453AFB4B8633E9B9C6F.ashx
https://www.dennys.com/assets/files/Dennys-Allergen-Guide.pdf
Don't stress too much about your slip-ups. You're still learning and you're still trying. You're doing great!
EDIT:
Dark chocolate is usually your friend. Skip milk/white unless you buy them from some organic place/wholefoods and it says 'vegan'.
And if you're going to a restaurant (and you know in advance, like a birthday, work christmas party etc.) call ahead and speak to someone about vegan options. If there's nothing on the menu, the chef will prepare you something if s/he knows when you're coming. I've done this heaps of times and when I've spoken to the chef directly they are generally quite enthusiastic as they get to make something different. I've never had a bad vegan meal doing this.