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Is it worth selling my iPad Air 2 and getting a iPad Pro 9.7 inch?
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There are only two reasons why you would benefit from the switch. 1)If you NEED 256gb of storage, or 2)You intend to use the ASK and or Apple Pencil. You've already mentioned the first one so I'd say go for it.
Aside from the additional storage you were wanting, that Pro 9.7 inch only offers true tone display, quad speakers, and of course Apple Pencil support. Those are the three standard features that are likely to separate it from the Air2.
Aside from those features listed/memory, the Air 2 Easily competes with the 9.7 pro.
You have omitted a crucial piece of information... the storage capacity of your current iPad air 2.
Ah, thanks... that helps.
Given that, I don't think it is worth upgrading to a 256GB 9.7 iPP at this point in time. First, you will get killed on the resale of the 128GB Air 2. Resale values have seriously dropped on iPads since stores have started regularly discounting iPads. The hardest hit on resale have been the higher capacity models.
Second, there are some serious possibilities of new iPads being released/introduced in March 2017. One of them is supposed to be a 10.5" iPad Pro... smaller bezels but in the same form-factor as 9.7. You might want to wait to see what shakes out then.
Third, this is just my opinion, but I never had a good feeling about the 9.7 Pro. Something about the 2GB RAM, $100 price increase, and the timing of the release just felt a little "off"...like maybe there won't be a proper update to the 9.7 Pro. This is just my feeling so it really is not important in the discussion.
I too like to have all of my media with me on my mobile device, but there is no device out there that comes close to what I would need. So I've had to deal with the situation, using smart-playlists for syncing music, and manually selecting videos, comics, and other media to cover a wide range of moods I might be in.
As a temporary solution while you wait, you might want to consider the RavPower FileHub. (@M. Gustave turned me on to it) $33 at Amazon, and another $30-40 for a 128GB SD card to insert into it and you'll have another 128GB storage for use. It is no way as convenient as having all 256GB onboard, but I've been testing this combo out (as a solution to my mom's "iPhoto storage creep") and it works great.
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There has just been another thread asking for the upgrade experience from Air 2 to Pro. I suggest to actually read the forum and do a bit of research because the majority of questions around products this old has been answered and discussed to death.
The sound from the four speaker system is something that cannot be disregarded. I've owned the iPad Air before and it truly is a difference i.e. when watching movies or listening to music. The display is indeed very good and I am happy that they removed the ugly plastic piece covering the antennas from the cellular version. The best iPad ever.
128GB is a lot so no reason to upgrade. I have 128GB iPP 12.9 and I am not planning to store all of medias. I put all stuff into portable wireless hard drive with 500GB! Able to stream up to 6 devices at same time. Is it awesome? 
I would say no, iPads now really dont keep their value. Unless you really need the pencil support.
Air 2 and Pro are not that different in performance. Maybe if the Pro had 3gb of ram it may have been worth it.
Air 2 and Pro are not that different in performance. Maybe if the Pro had 3gb of ram it may have been worth it.
I went from Air 2 (9.7) to Pro (9.7) to Pro (12.9) all in one week. I got a deal on the Air 2, but ultimately wanted to replace my Macbook, so the Pro 12.9 was a much better fit for me. The 4GB of ram in the Pro (12.9) is very helpful for future iOS 11 and iOS 12 updates. I highly doubt I'll be willing to spend $1,000+ (ASK + Back Case + Pencil) on the new Pro 12.9 iPad in March.
Unless you need the stylus or keyboard, my answer is no. I actually did sell my Air 2 and bought a 128GB LTE 9.7". Not at all worth it.
If you asked this question earlier this year, I'd say go for it. But you should only have to wait a few more months for new iPads and 128GB is plenty of storage already. If that's really the only reason you feel compelled to upgrade, I think you can continue managing your storage a little longer and get a much better device.
Nope. The holiday sales on brand new iPad Air 2 have hammered resale value. Just wait for the Apple keynote in March.
Everyone keeps saying that it's not worth it because new iPads are coming in March... Does nobody take price into consideration? You can find good sales on the iPad Pro's right now--up to $150 off. You will most likely not find a sale on the next gen iPads for months after its launch.
But the current iPad will be even cheaper when the new one comes out.
I don't know about that. I got the 128GB iPad Pro 9.7 for $519 a few weeks ago (retail is $699). Apple products don't get discounted by much after the next models come out.