I'm not saying it isn't worth it to anyone... just that it wasn't worth it to me. I used that $300 to upgrade the AMD 8150 in my desktop to a Skylake i5 6500. I got better returns that way. If I were done with college and had a real job, I would have preferred having the i7, but $300 matters a lot to me at this point in my life.
If you don't do at least some mid-level gaming though, I don't think you'll need the IRIS graphics. The HD 520 that comes with the Skylake i5 is already almost a 40% upgrade from the HD 4400 that comes with the Haswell i5. I haven't really had much time to test the SP4's gaming ability compared to the SP2, but I have loaded up GTA Online, and the SP4 is just baaaarely able to keep up, which is really pretty surprising. Death matches and other closed world activities works great, but I need to do some tweaking to get the game working in the open world. I can play Fallout 4 on my SP4, which is pretty awesome, and Project CARS runs much better on the SP4 than it did on the SP2. All Blizzard games run pretty much seamlessly. Elite: Dangerous runs fantastic on the SP4, and my favorite game to play in tablet mode, Automation, runs fantastic even at 50% CPU.
Based on my performance with the i5 in GTA Online, I think the IRIS graphics would probably be just enough to bump up performance enough to run nearly any modern game on minimum settings.
The stylus on the SP4 is way, way better than the stock stylus on the SP2. I upgraded my SP2 stylus to the 3-button Lifebook stylus, and liked it a lot better than the stock one, but the SP4 stylus is still way nicer. I do miss the 3rd button a lot in CAD work though. The tip is night and day, completely different. The SP4 tip drags across the screen similar to how a pencil drags across paper. Artists far prefer this to the plastic tip on the SP2 styluses. I tended to prefer the SP2 stylus tip, because it was more effortless when taking 4-6 hours worth of notes in a day. The SP4 tip tends to fatigue you more after long use... but for accuracy, it is worlds better, I wouldn't want to go back now. I hear reports that the tip is more fragile, and while I can see why it would be, I've dropped it and smacked it against things a couple times and not had an issue.
But I haven't had any of the issues people complain about on their SP4, other than sub-par battery life. Running the processor at 50%, I can barely get 8-9 hours worth of life out of it. Using Microsofts automatic power management, I was getting about 4.5 hours. I also don't use Microsoft Hello (yet) and it apparently kills the battery even faster when in sleep mode. Sleep mode is another feature I never use though. The SP4 starts up so fast, I just power it down when I'm not using it. So while I haven't had any serious problems with my SP4, I also don't use the features that tend to cause the most problems.
I like the idea of the iPad, but I've never owned one. In my opinion, they are great toys, with some production uses. I think they are far too expensive based on their usefulness though, so I've never been able to justify the price. I might have gotten an iPad Mini had Windows 8 not come out around the same time, as the price was more in line with what I thought the iPad was worth. I say all that to provide you with the background to understand my opinion of iPad's as a whole. I think they're cool, but I don't think they're nearly as cool as Apple wants to charge for them.
That said, I think the iPad Pro is rather absurd. With a stylus and keyboard, the base model will cost you over $1000! That model comes with only 32GB of hard drive space, which is not expandable, and you won't get half the useability of the Surface Pro 4 m3 at the same price, and the m3 would have roughly the same performance your SP2 has, minus 4GB RAM. The SP4 m3 also comes with a 128GB hard drive, which is expandable to 256GB with a $60 microSD card. I run all my Steam games off my microSD card on my SP4, so you aren't limited in how you can use that memory. So yeah, the only reason I see for you to get an iPad Pro is if that's the only way to keep your wife happy. As far as production ability goes, it's inferior to the SP4 in every way.
TLDR:
For home use, nothing beats a desktop. You could build a beast of a machine for the $1200 you would pay for the 8GB i5 SP4, and have money left over to get a 1080p 40" flat screen to hook it up to. The SP4 shines for mobility, digital art creation, and productivity on the go. With the iPad Pro, you're paying for a really nice, ultra expensive 12" screen. That, in short, is the summation of my opinion on the matter.

Hope it helps, and lemme know if you have any other questions.