I recently upgraded from an HTC One X Android smartphone, to a brand new Samsung Galaxy Note 4 Android smartphone.
Before Android, I had a Windows phone and before that, many versions of PalmPilot. I've used Microsoft Outlook for 20+ years with a variety of different email accounts, and for the last 10 years a standard Gmail account. With both the Windows phone and Palm, I could sync easily my Outlook Calendar, Contacts, Tasks and Notes to whatever device I was using, for free. All that changed when I went Android (which I love in every other respect, except this).
Once I got my first HTC Desire in 2010, I suddenly found that the only way to sync using the provided HTC Sync Manager software was via USB cable, but it would only sync Outlook's Calendar and Contacts. I've worked around that by finding other apps such as Evernote to handle Tasks and Notes. (It also repeatedly attempted to suck every image and music file from my PC onto the phone, which I fought on an ongoing basis, but I digress).
My biggest (only) reservation about moving to Samsung hardware was their crappy sync software, Samsung Kies. I tried helping a friend set this up for her Samsung a year or so ago - it worked for a week and then came up with a random error message - when we Googled that message, there were 40-odd pages of people reporting the same error - AND NO FIX. A simple Google search reveals the extent of the horror that is this software, so that was never going to happen.
You'd think if you had a Microsoft PC with Outlook, a standard Gmail account and an Android phone, syncing the Calendar, Contacts and Tasks from PC to phone should be easy, right? Nope...
My desktop PC is a rather old Windows 7 64-bit. Back in 2010 I thought I could just sync my Outlook calendar into Gmail, then sync the phone to that. Nope. Google and Microsoft do not want to play nicely so you can't do that with a simple Gmail account - even now, you need to have Google Apps for Work, Education, or Government. You can't even buy this software - instead you have to upgrade your Google account to a paid version.
As I refused to consider using Samsung Kies, that made a direct USB <-> phone sync tricky.
The only option was third-party software. Unfortunately, I tried this back in the HTC days and some of the third-party apps install their own Calendar and Contacts apps onto the phone, but other apps look for the default calendar and contacts apps. Then Gmail didn't like what Outlook was serving up and dropped data... it was awful.
Anyway - the good news is, for the last month I've been testing AkrutoSync and it seems to be working beautifully. It automatically syncs any Calendar, Contact, Task or Note I add to either PC or phone, via wi-fi and almost immediately, and I don't lose any data in the sync process. The data goes into the default Samsung S-Planner, S-Notes and Contacts apps on the phone, and into the correct Outlook folders on the PC.
There are only 2 downsides to this software and they're fairly minor for me, but may be deal-breakers for others. First, AkrutoSync is only for Samsungs, which unfortunately rules out HTC if I ever decide to return there.
Second, to make this work, it is necessary to create a Microsoft Exchange Active Server account on the Samsung, and all the "phone" data is within that account. The problem is that if I want to invite anybody to a meeting request, it comes from that account and not from my "real" email address. The workaround is to only send meeting requests from Outlook. Having Tasks and Notes back on my Android smartphone though, makes that little glitch worthwhile for me!
** Update 2 September 2015**
Have recently discovered another issue. AkrutoSync takes port 80 on your PC and this port number cannot be changed. As a web developer, I have run WAMP for many years on my PC, configured by default to port 80. While I can change WAMP to use a different port, it means going through every setting and bookmark and manually changing them all to reflect the new port - a big job. Skype also uses port 80 by default, but Skype allows you to change to another port so this was a relatively simple fix. AkrutoSync needs an option to change the port away from the default to avoid conflicts. Currently I need to shut down AkrutoSync to do my web development work.
