Want to sync without loosing a ton of data (again)

Question

I'll apologize in advance for such a long post, but I'm not sure what else to do. iTunes, during my version upgrade, lost months of my personal data.
Question:
I'm wondering if there is a way to back up my data on my phone and be really sure it (my data) is properly backed up? Is syncing the same as creating a backup file? I'm not in the mood to try to backup or sync only to find out that my data is lost again. I've spent hours searching for answers since I'm trying to avoid a repeat.
What I'm trying to do:
I don't want to unleash iTunes to backup and then sync out of fear I'm going to lose some or all of my data. I'd like to backup my phone and be sure it's really backed up, so if my sync sinks me (again), I'll actually be able to recover my data. I try to sync to Windows7's Contact list. iphone's on 4.2.1 and iTunes is on Version 10 I think it's an iphone 3G and I've had it for a couple years.
Background:
I use my phone for a small business where I'm on the road. So I have some contacts, calendar entries, and notes that are pretty important to me and really need it in my phone and not in my computer.
I sync infrequently because of what I listed above combined with the fact that syncing is painful. It creates duplicate contacts, which is a well documented problem on these boards, but with no solutions I can find for my situation. (I use the Windows7 Contact list). iTunes will also neither sync my calendar nor notes, which I can understand, since it's got to be several hundred kilobytes of data which is clearly a challenge for the developers at Apple. I have historically hooked up the phone, agreed to let itunes download and install all it claims it needs, and walked away for a half hour or so. Then I spend another 40 minutes deleting duplicate contacts.
My last sync (2 weeks ago) deleted all my personal information back to January. It involved an iTunes upgrade and I lost some photos, calendar entries, recent call list, notes, etc. I spent 3 hours with Apple tech support only to conclude that the backup file was not stored correctly. Apparently iTunes writes the file then wipes out the phone. At the end of the process, it was unable to restore it (some error said there was already a sync in process, or something like that). The backup folder had the correct date and time stamp, but upon reviewing its contents; it appeared to be incorrect. My data was lost and the Apple tech support apologized.
Now I'm not sure what to do. I may resurrect my palm pilot, since it sync's everything and, in more than 10 years, never lost any of my data. I'm not too keen on carrying around two devices, however it may be better than constantly fighting with my iphone. Sorry for venting.

Answer 1

iTunes updates your iPhone's backup as the first step during the iTunes sync process and you can manually update your iPhone's backup without syncing by right-clicking on your iPhone under Devices in the iTunes source list and at the menu window that appears, select Backup.
This link provides the data that is included with the backup or that should be included with the backup, which is substantial.
http://support.apple.com/kb/HT1766
I use my phone for a small business where I'm on the road. So I have some contacts, calendar entries, and notes that are pretty important to me and really need it in my phone and not in my computer.
Understood and I do the same, but what would happen in regards to this data if your iPhone were lost or stolen?
iTunes will also neither sync my calendar nor notes, which I can understand, since it's got to be several hundred kilobytes of data which is clearly a challenge for the developers at Apple.
The iPhone supports syncing calendar events, notes, and contacts with Outlook 2003, 2007, or 2010 with Windoze. It is enough of a challenge trying to sync this data with the definition of a bloated application that is Outlook, much less trying to do the same with the Calendar app included by Microsoft with Windows as well.
Most the well documented problem with duplicate contacts on this board has to do with those with a MobileMe account who are syncing contacts over the air with the account and syncing contacts direct with a supported address book application on their computer via the iTunes sync process which will cause duplicates on the iPhone.
Are the duplicate contacts caused when syncing contacts with the Windows address book on your iPhone only, or in the Windows address book as well?