How can I sync contacts and calendar via iTunes 11.1.8 to iOS 3.1.3 (iPhone 1)?

I am proud owner of an iPhone 1 and it still works fine, but runs on iOS 3.1.3. I updated my 2 year old iMac to Mac OS X (10.9) and I am now using iTunes 11.1.8. Actually, I bought my iMac because I was so enthusiastic to see how smooth syncing with my iPhone worked. Now, since OS X, I can not sync calendar and contacts anymore. I had to reset my iPhone and start from scratch, so contacts and calendar are empty.
Sync via iTunes does not work anymore because Apple deleted the direct sync function and my iPhone's iOS does not support iCloud.
Sync via CalDav does not work, beause for some reason my iCloud account is not approved when trying to create it in mail/calendar/contacts (I tried several times, crosschecked, all data appear correct to me and work in the browser access).
Sync via Google does not work, because obviously, my iOS does not support their calendar and contacts function.
Sync via Windows PC might work, but I would have to set one up from scratch.
Downgrading to iTunes 10.7 failed, because OS X didn't allow it. Downgrading the Mac OS might be an option, but I am already running e.g. Books and using it a lot.
Any help is welcome.
Iris
P.S.: I still remember Steve Jobs saying "it simply works!"

Thank you Meta, but I could not get the calendar and contact sync with Gmail to work. Apple support already suggested to use Google or a Windows PC. Maybe I should actually reset and try my old Windows PC. Seriously, ... can this be the solution after a Mac OS update for pure Apple users?

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Brij011 wrote:
I think I understand now, it's nothing to do with syncing music - everything is synced through iTunes. Have I understood properly?
Yes. Including music.
Brij011 wrote:
This could be a major blow for me as I'll be using the iPhone mainly for work so I will have to Sync with the PC. If I understand this correctly, once I decide to sync with Outlook on the PC as the main priority I can no longer sync with the Macbook?
What if I ditch iCloud and sync everything through USB?
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Ok, to quell the confusion on this issue let me fix the general errors with this so others here can see why this is caused and how to fix it.
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Hi Guys
Look, I don't know if this will help perhaps.
We use Novell Groupwise (a stupid system if you ask me) at work and I finally got Outlook and Groupwise to be happy together concerning email. None of my problems were Outlook or MS issue, everything was Novell's fault. Then I had a lot of trouble getting my N8's calendar to sync to Outlook from Nokia Suite v 3.4.49, again this was Novell's fault.
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I had the same problem, and decided to look into it last night.
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