I think it's "okay" to buy leather second hand or as a hand-me-down. I once received a very beautiful wool scarf from my aunt as a hand me down. She is not vegan and didn't use the scarf anymore, she thought I would like it and I did. It's been many years and I still use it. She didn't know it had wool in it and doesn't really understand it. She also gave me a leather jacket for the same reasons. It didn't fit me so I gave it to someone else (w/ her permission) and they still wear it, too. I still have 2 pair of leather boots from before I went vegan. I would not purchase them again, but I'm not going to give them away "just because". They are beautiful boots, they fit me well and I'll never find another pair like this so why put them away? They are my "nice boots" and very timeless, so they will last me until I can't put my feet into them anymore probably as an old lady lol.
It's different for everybody, there is no right or wrong here. Vegan leather is not all that great, so I understand if people buy leather boots that last a very very long time in stead of plastic vegan leather boots that you have to re-buy every 6 months. There is something to say for both sides. Personally I don't feel comfortable buying new ones, but I understand if people (for reasons i just mentioned) do. Second hand is a great option too and sustainable, too.
Not me defending Maddie here though. Just general talk.
Feeling bad for Roxie the dog. I don't understand why she has a PT and a fitness bike, if you have bike why can't you just run, walk or bike with your doggie?