"Our lives our filled with enough real decisions without the need for inane and subtle product ones."
Considering the length of time we spend with our gadgets it pays to spend a bit of time in those 'inane' decisions. However, if you're a light user and just want something that works you can always choose based on price. It's really not that hard.
"With the iPhone I'm now forced to regret the decision either way."
But are you though? Let's imagine for a second that the iPhone 6+ didn't exist. Is the iPhone 6 enough of an upgrade for you to want it? The obvious upgrade path is iPhone 5 to iPhone 6, if you've never wanted a phablet then the iPhone 6+ is not for you. There, I made your decision for you.
That's the point, that it does exist. I don't regret the other iPhone 5's because they actually don't exist. Since the iPhone 6+ actually does exist, developers will start programming custom superior landscape layouts for it that will serve to continually remind me I don't have it.
Had the only difference been physical size, the decision would be easy like you describe, I'd be measuring on one variable that I know how I prefer. (Note that this could be similarly fixed by apple choosing to offer the landscape modes on the 6 too, then it would just be battery and camera that are worse, of which battery is understandable).
"I don't regret the other iPhone 5's because they actually don't exist."
Except that they do exist (i.e. iPhone 5C). Perhaps you didn't face this dilemma with the 5S vs. 5C because it was clear which one was seen as the "best". It's the status symbol aspect.
Phablets are a niche market, if you have never wanted a phablet then the 6+ is not for you. The flagship model is the 6.
As for the features you'll be missing out on, do you have the same feelings about the superior features you can find on non-Apple phones? PureView from Nokia is far superior to Apple cameras, you can find Android phones with far better batteries, etc... Why is it only an issue with Apple? Again, I suspect, it's the status symbol aspect.
Once again, you seem strangely convinced that I am obsessed with the "status symbol aspect" despite my repeated listings of the differences in features I care about. I'll try once more: the iPhone 6 is smaller, which I consider better because I have small hands. The bigger one has iPad-style landscape layout and a better camera that I care about. Notice how neither of those have anything to do with impressing anyone with my status. Notice also that I don't care that one happens to be called a phablet: it still contains features unrelated to the size that I want and don't understand why they left out of the smaller one, and I also fear the fragmentation of the app market for things designed for the bigger screen and arbitrarily not available for the smaller one (as has already happened in Apple's software).
And I absolutely care about the discrepancy of features with Android as well. I happen to stick with iOS since I develop on iOS, of course I'm sure you'll now respond that this is really subconsciously because I want to have the status of an obj-c programmer or something.
"I also fear the fragmentation of the app market for things designed for the bigger screen and arbitrarily not available for the smaller one (as has already happened in Apple's software)."
That could happen, but if it happens a lot I'd expect Apple to change their app approval guidelines. iOS now supports dynamic layouts AFAIR so it shouldn't be a big issue for the better developers.
As for your continued phone upgrade dilemma, if you're an iOS developer there's a good argument for getting both (if you can afford it), but aside from that...
Have you used a phablet before? Small hands may not be an issue, speaking anecdotally phablets are relatively popular in Asia and Asians seem, on average, to have smaller hands than Americans. Why does this popularity exist? I'd suggest it has something to do with where you use your phone and what you use your phone for.
Ask yourself two questions...
1. Do I mostly use my phone whilst standing up or sitting down?
2. Do I communicate using voice calls much?
If you mostly use your phone sitting down and don't use the voice call features of your phone much, consider a phablet. If you're often using your phone whilst standing up, consider the smaller phone. If you use voice calls a bunch, but mostly sitting down, it's mostly personal preference (I mean, it's all personal preference, but the answer is less clear cut).
Perhaps the only way you'll resolve this for yourself is to try a phablet for yourself and see if you get on with it. Do you know anyone with a Galaxy Note?
"With the iPhone I'm now forced to regret the decision either way." But are you though? Let's imagine for a second that the iPhone 6+ didn't exist. Is the iPhone 6 enough of an upgrade for you to want it? The obvious upgrade path is iPhone 5 to iPhone 6, if you've never wanted a phablet then the iPhone 6+ is not for you. There, I made your decision for you.