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I'll post what I posted in another thread:

"If I had to guess based on Apple's history and the current climate, I'd say a year or more before a new iPad Pro. Their current chip in their iPad Pro line is currently more powerful than any Tablet on the market and most laptops. This is more like an 'S' upgrade. In my experience when Apple does this, it's to buy more time while they work on a major upgrade of said product, while at the same time giving it a refresh to encourage more buyers. With the release of 13.4 and mouse support, plus the Magic Keyboard, they've done just that. My guess, March or Sep of 2021. The only other possibility I could see would be a new iPad category all together that gets released later this year in response to Microsoft's Surface Neo. But as far as the iPad Pros go, I believe what you see is what you get for at least another year"

So in short, if you want or need one now, why wait? As other posters have said, I wouldn't get into the what ifs waiting game. Trust me from experience, that can drive you crazy. There will always be new tech. I have a 2018 11". I just upgraded to the 2020 12.9" because my needs and circumstances have changed and I wanted the bigger screen. Although many say it's not worth the upgrade from the 2018 models to the 2020, the big screen was important to me at this time. I'll worry about what happens in a year or so when the time comes.

My opinion is there won't be another iPad Pro Model for at least a year or more. I feel what you see is what you get for the foreseeable future. I do see Apple working on a new category of iPads similar to how they did with the iPhone when they released the iPhone X. If you recall, the iPhone X was a completely new redesign. It was in a category by itself. Now their standard and pro models are designed after this concept. I see that happening with the iPad line. Apple will release a 5G, mini LED, possibly foldable, iPad that's in a category of it's own. Then months down the line they'll model their Pro and Standard models after this design. Just my opinion.
 
Always something new around the corner after all...this iPad was suppose to be out October 2019 and didn’t land til march 2020 so nobody knows when the next one will be out
 
I totally agree with this, the 2020 iPad Pro is a beast. If there is another iPad Pro launching in 2020 end or 2021, it will obviously be faster and sport some amazing must-have feature.

But in the end, it all depends on your needs. Do you really need something super fast right now or you need something super-duper fast that may or may not arrive in a few month's time.

If the 2020 iPad Pro specs satisfy your professional and personal needs then go for it. But if you will be making a compromise because there's nothing better in the market, then you might wait.

Agreed... the wife's and mine arrived and were set up last night. Pretty beastly upgrade coming from a 2017. No more bezels and touch ID.

I did the same thing with the phone though... kept the 8 Plus a few years until I upgraded to the 11 a few months back. I fully expect to be good to go for the next 3-4 years at a minimum with both the phone and the new iPad.
 
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Always something new around the corner after all...this iPad was suppose to be out October 2019 and didn’t land til march 2020 so nobody knows when the next one will be out
The prevailing rumour (from May 2019) for this iPad Pro refresh was late 2019 to early 2020 manufacturing. So it seems like it’s right on time, since shipping is usually months after manufacturing begins.

For the record though, based on the rumours, I was predicting February 2020.
 
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I am also in the same boat as the OP. The last iPad I own was the 10.5 iPad Pro in 2015 or 2016 I can't remember and I sold that last year. So now my main consumption device is my early 2015 12" Retina MacBook. I've been deciding whether to replace it with a new 13" MacBook Pro or a 12.9" iPad Pro.

With the new magic keyboard and trackpad/mouse support it might as well replace my MacBook, and plus the built-in facetime camera on the macbooks still haven't been updated. They are still 720p. Even the iPad and iPhones have much better quality cams. That's a downside for me since I use FaceTime quite often. However, the one thing I dislike is the placement of the front facing cam on the iPad's. It doesn't make much sense to have it where it is. Especially if you're going to be using the iPad in landscape mode with a magic keyboard. It makes much more sense to position the cam on the top. I was hoping that Apple relocate the front facing cam in the new 2020 iPads but they still haven't.

Also I'm not sure if I should wait until this fall for an updated version of the iPad Pro which I've been hearing about. I'm not sure if there even will be a refresh coming and if so, I'm not sure if the extra features or upgrades will be worth waiting for.

But whatever device I choose on buying, I plan on keeping it for as long as possible before updating to a newer model, which is about 6-7 years.

I'm leaning towards the 12.9" IPP 512GB model.
 
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