Saw this thread earlier and wanted to chime in because I had a similar frustrating experience when I got my X-S20. I bought the Peak Design Cuff Camera Wrist Strap thinking it would be perfect, but unfortunately, the quick-connect anchors kept getting caught in the screen hinge mechanism when trying to fold it out quickly. It was not as good as expected for street shooting where speed is everything. Then I tried a cheap hot-shoe thumb grip, but the clearance on the X-S20 top plate is tight and it blocked the rear command dial access. I ended up stripping the setup down. Honestly, the best fix for the chunky feel was adding the SmallRig L-Shape Grip for Fujifilm X-S20 4231. It adds about 79 grams, but it shifts the center of gravity just enough when using the 27mm pancake, and it gives you a solid bottom mount for a hand strap.

Just saw this and wanted to share my setup. Since youre running the 27mm pancake, the X-S20 can actually feel a bit unbalanced because of the deep grip compared to the old X-T30. Instead of a thumb grip, you should look at a base plate to give your pinky some purchase without adding real bulk. Here are a couple of specific items that work well for this setup:

• SmallRig L-Shape Grip for Fujifilm X-S20 4231: It adds only 78 grams to the setup but gives you a solid silicone grip extension and an integrated Arca-Swiss plate. It makes holding the chunky grip much more secure during long street walks.
• OP/TECH USA Cam Strap QD Wrist Strap: This uses thin but incredibly strong loop connectors that wont bind up the flippy screen mechanism like the thick plastic quick-release pucks do.
• B+W 39mm Master 010 UV Filter: Since you are doing street photography in Chicago, wind and grit are real factors. This filter uses MRC nano coating which has a 99.8% light transmission rate, so you wont lose any optical quality on that sharp little pancake lens. For under 100 bucks total, these upgrades keep the camera protected and ergonomic without blocking the articulation of that screen. Have a great time in Chicago.

TL;DR: Skip the thumb grip since it can block the dials, but definitely get a bottom-mounting wrist strap to keep that flippy screen clear. When I first upgraded to a chunkier camera body, I threw a cheap thumb grip on it and immediately regretted it. It scratched up my hot shoe and blocked the rear dial. I also learned the hard way that standard side-mounted straps constantly block the articulating screen when you try to flip it out. You might want to consider a strap that mounts to the bottom tripod socket instead. Be careful with those thumb grips, they often do more harm than good on these smaller bodies. Let me know if you need any other Chicago prep tips, I can help you out with some great spots!