[Samsung Galaxy Tab S8] SavXL:
I use the Tab S8+ as an upgrade over my Tab S4 from a few years ago and I'm just saying that I'm never looking back. The bigger screen is amazing for media consumption, drawing, editing (whether it's photo or video), multitasking, etc. I don't output to a monitor or TV very often, but if I do, the experience is pretty good. Dex has come a long way over the past couple of generations and device revisions and is almost good enough to be a laptop replacement (for some, not for all though). I'd only recommend the Ultra if you SERIOUSLY need double the ram, a bigger screen ( 2.2" bigger than the S8+, 3.6" bigger than the S8), and the second forward-facing camera. The performance is practically the same for all three Tab S8s, the only difference being the size, cameras, and ram. 8GB is enough for most people, but if you genuinely need more, then I'd spring for the S8U, but if not, then either the S8 or S8+ is perfectly fine. I chose the S8+ for the bigger, more vibrant, super AMOLED screen. After daily driving a device with an OLED screen, I can't go back to LCD, but I've heard the TFT LCD on the S8 is pretty good for being an LCD. You do miss those deeper blacks and some color fidelity though.

Edit: I thought I should answer a few of your questions and address some of your concerns. ;)

- The UI is still pretty bloated (especially if you have an S8 with 5G capabilities like Verizon), but it's a lot more manageable than before. You can disable a lot of apps that you don't plan on using, as well as uninstalling their updates, not allowing them to change system permission or have any permissions at that, or even straight-up hide them from the app drawer if you're using the OneUI Home launcher. You can even remove them via ADB commands if you hook your tablet to a PC as long as you input the right commands.

- The aspect ratio of all Tab S8s is 16:10, not 16:9. The tablets are a little wider to account for that. As a result, it's not going to cover the entire screen when outputting to an external display, and yes, it'll only be at 60hz.

- The Tab S8 line will continue to receive software updates for the next five years (until 2027), so we will probably get the next two or maybe three next versions of Android, as well as semi-frequent security updates and patches. We'll be up to date for quite a while, at least until the next Tab line comes out.

- Not having a headphone jack is one of the main reasons why I didn't spring for the Tab S6 line back in 2020, but times have changed and now I've found pretty reliable alternatives to continue using wired headphones, use the mic attached to those headphones for calls and audio recordings, and to charge at the same time. I'll use the ANKER USB-C Hub mainly for displaying to an external display, but I did use it for simultaneous wired headphones and charging until I got the Stouchi USB-C 3.5mm Headphone and Charging Adapter. This dongle has served me well for some months now and while it can give me some occasional charging issues (mainly due to my poor positioning), it's a quite durable and serviceable dongle. Not to mention that if you ever have issues with it, customer support responds via email very quickly, and has a quite friendly staff team that'll help you out.

- The tablets really aren't as large and unwieldy as many people try and make them out to be. Maybe it's just because I have big hands or have no problem carrying reasonably heavy things, but it's genuinely not that bad. With the specs that are in these newer tablets, I'm surprised that they're not heavier. The S8+ is 1.25 lbs (around 0.6 kg) and is quite thin and quite lighter than it should be given what's inside and how well they perform. Adding the cover case included with the official keyboard for these tablets (not the slim one, as those are one piece as opposed to being made of a magnetic back cover with an S-Pen cover and a keyboard attachment) does add a bit of weight to it, but not enough to cause any sort of strain.

- I use Sketchbook for drawing, but I've been recommended Medibang quite a few times since it has a lot more creative tools that you can use. Both are free as far as I know.

- Samsung Notes has a feature where it can turn words you've written down with the S-Pen into regular text. I believe there's also an S-Pen related app that you can use in its little sub-menu (when you press the button on the S-Pen close to the screen), but if there is, I don't use it very often. I just stick to Samsung Notes since it seems like a dedicated app for exactly this purpose. You can even backup notes you've made to the cloud if you log in to your Samsung account. Quite the handy application if I do say so myself.

It may be a lot to read, but I hope I helped you in your decision a little bit. These are some pretty great (if a little pricy) devices, and any of them would be a great upgrade over your previous (or I suppose current) Samsung tablet. :)