First of all, I love your thread title reference.
I wouldn't be overly worried about the YSL. I have a black YSL monogram cabas as one of my workhorse bags and it's holding up beautifully. I like the bag you show but make sure to try your things in it. The small size and rigid shape may make it less roomy than expected.
I don't care for the Burberry. It looks a little meh. I think there are better options. I went through a LONG search for this type of bag and here are some bags I considered.
My first choice for your would be the LV LockMe II BB in Noir. I just bought this bag and
LOVE it!
And I'm not usually an LV fan. But this bag won my heart!!! The long strap is removable so you can use it as a clutch or with the small chain strap. The leather is positively scrumptuous!!!!! Probably the best calfskin in my collection.
My second choice: I'm slowly falling hard for the Fendi Peekaboo. Fendi quality is great, this has a top handle and a strap and the leather is beautiful. I can absolutely see this bag in a larger version in my collection down the road
I also like the LV Alma BB in epi and am thinking of getting this in a bright color. It holds far more than you think. It has a top handle and a shoulder strap. It has a long history and will likely never go out of style. The drawback for you is the leather isn't soft. But the tough nature of the epi may be worth it.
A girly, iconic option is the small Lady Dior. I go back and forth on this bag. I think I'll eventually own one but haven't taken the plunge. One day I love it. The next it's too twee. The leather is great, it has a top handle and an optional strap. It also comes with choices in hardware. I think it's the medium that is hard to get into but the small isn't? Someone on the Dior forum will have more intel. If you buy preloved, there are a ton of pristine black LD's on the market at a good discount.
Being a die hard Chanel girl, I have to mention the Chanel boy. It doesn't have top handle but it comes in luxurious lamb and a variety of hardwares. This picture is the small size but I think the old medium would be better for your needs.
And, lastly a Chanel with a top handle is the Chanel coco mini. I'm not familiar with this bag but have seen some lovely reveals. I have to be honest. I worry if this bag will look dated in a few years but what do I know? I could be an it bag for the next 30 years. LOL!
Hope this helps! Let us know what you get!