I'm going to have to checkout that targus backpack, my old swiss backpack is finally giving up the ghost after about nine years. I got a couple of cubes as well, plus some flat zipper pouches for paperwork, receipts (helps when the backpack gets wet).
I didn't see a usb hub or a network hub in your list. They are in my must haves. I use the hub all the time. Plus I carry a couple of USB Ethernet dongles. Can't go anywhere without a headset/mic for online meetings.
I got the extra monitor. Love having it, but I got an AmazonBasics Adjustable Tablet Holder Stand https://www.amazon.com/gp/product/B006ZT4VA0/ref=ppx_yo_dt_b_search_asin_title?ie=UTF8&psc=1 much better stand.
or combine it with this to make the footprint smaller https://www.amazon.com/AmazonBasics-Adjustable-Tablet-Holder-Stand/dp/B006ZT4VA0
meh.. this is better with adjustable angles.
http://www.amazon.com/AmazonBasics-Portable-Fold-Up-Travel-Samsung/dp/B006ZT4VA0/
I have the Moko Slim-Fit Multi-angle Folio Cover Case and it has a cut out area so you can attach the pogo connector with the case closed. If you really want to have it connected while in a standing position, you might consider getting a tablet stand like this one that leaves room for the connector. You might have to leave it hanging over the edge of your shelf or desk, but it would work.
But, no, I do not believe there are any 90° pogo cables and even if there were, I doubt they'd be flush enough to fit in your case.
I use one of these stands. It works well enough, but still slips a tad under heavy tapping. My desk has a glass top though so a different surface might grip a bit better.
I bought this folding iPad stand made by Arkon. (I used it to display a custom keyboard on a shelf). It cost $14 at the time.
https://www.amazon.com/dp/B000CKVOOY/
Later, I needed a second one (for another keyboard). I saw this Amazon Basics folding iPad stand that looked remarkably similar but for a few dollars less:
https://www.amazon.com/dp/B006ZT4VA0/
Out of curiosity, I bought the Amazon Basics one and compared it side by side with the one by Arkon. They are exactly the same!
AmazonBasics Adjustable Tablet Stand https://www.amazon.com/dp/B006ZT4VA0/ref=cm_sw_r_cp_apa_i_EDtwBbF3EAAA4
Not as low profile, but this stand also works. It doesn't touch the front, so it works with the screen up or down. I'm able to use a cable with an angled plug in the bottom USB-C port.
Not the same stands but this tablet stand from Amazon works great for keyboards.