Wow martti, looks like you've been around the block a few times! Thanks for the detailed account. I salute, appreciate, relate to, sympathize and respect your long path of experience. This is pretty familiar to me as well. I went through a similar experience multiple times with various clients and friends. (I'm usually either the 'paid consultant' or the 'tech-geek buddy expert'.) There are few of these productivity tools I haven't seen at some point. They all had their strong points and problems. Complicated and difficult to get the promised benefits from in one way or another. And add some of the other pieces that you may have missed like making sure the Palm phone device works correctly with various Real Estate apps and services. For quite a while, eSync required the Palm device to sync with another device in order for the realtor to get codes or unlock house key boxes. When that didn't work right, that was fun! (Sort of a mission critical thing for realtors, being able to unlock a house for a potential buyer.)
Add in a little Windows Phone and a lot of Blackberry and we have similar paths. My thing is that I experienced a lot of the same things you did except I thought the iPhone was a very expensive toy in the beginning with the 3G. It lacked almost all of the features of other phones, it cost a lot and when people tried to jailbreak it to get many of the features it lacked, Apple + ATT (with their years long exclusive contract) literally bricked the phones with updates. I was astounded that thousands of buyers tolerated this, actually felt ashamed and went back to the store and bought yet another expensive replacement iPhone instead of rebelling and kissing Apple goodbye by tossing the limited (now bricked) and expensive iPhone in the trash. After all, they just wanted to reclaim functionality that Apple omitted. This is a big reason why I don't buy Apple products. They are not very nice to their customers or the closed ecosystem and app developers that embrace their products. A LOT of iOS app developers lost their shirt when Apple would arbitrarily deny them Apple App Store access (or kick them out with no warning) for literally no reason or explanation. After months of app development on a given app, Apple would put them out of business before they even had a chance. This while other ridiculous FART apps, etc would be on the app store with no problem at all. So honestly, I just didn't want to support that behavior with my dollars.
Besides, I was very happy with my Blackberry. When my wife got the iPhone 4, I watched her for about a year and things seemed to improve with the iPhone and she liked it. Before that, we had both always had the same phone so it was easy to support. So I got an iPhone 4S after my Blackberry finally started giving me trouble (after 3+ years). Wow, what an adjustment. Productivity went down. Email/Messaging went out the window. It became just a read it if I need to but otherwise never use thing. Texting was good as long as I didn't want to attach a picture because iOS still didn't support that. Content consumption was good when I wanted to watch videos, etc which I rarely did/do. Lots of useless game apps was good. Photography was good along with all the app support which was the main reason I decided to try an iPhone. Voice calls were OK but call quality wasn't as good as the Blackberry. I got dropped more.
I was frustrated with a lot of things that Apple simply would not allow to the app developer with iOS. For instance, there was no way to have call alerts anymore if I missed a call. And the iPhone didn't support obscure (sarcasm) media formats like MP3. So all my custom ringtones and music that were in MP3 format were now useless because I didn't want to spend a lot of time converting them to AAC one by one. I also got tired of using the absolutely worst application every made - iTunes - to put files, music or whatever on the phone. Before with the Blackberry (and now Android) all I had to do was connect the Blackberry or just about any other phone to the computer with USB and drag stuff to it like any other external drive. In fact, way after I had moved to Android a couple years later, my wife finally gave up on her iPhone after syncing with iTunes totally wiped her phone of everything and she lost a LOT of important notes, files and other stuff. She was livid. It wasn't the first time I had seen this having supported clients having gone through the same thing with their iPhones. She was amazed at how easy it was to put stuff on her Android phone when she realized iTunes wasn't required anymore.
Most folks that I know or support, after all this time, that either own/use or have moved away from Apple products understand the true nature of Apple's plan. It's about locking you into a closed system that Apple controls for the primary reason of pushing you into buying content and apps from the various Apple stores. The devices are very expensive and Apple makes a LOT of money. Once they see that, regardless if they still use Apple devices, they understand the bigger picture.
I'm not saying Apple devices aren't really pretty, really elegant and don't give a good experience to the user, I'm just saying that I personally think the experience is too expensive and limiting for what Apple charges.
With Apple, it's not just the device, it's the whole experience. That's what most people don't understand.
