Upgrading iMac Quad Hard Drive

I am finally going to place the order for the iMac 27 in Quad Core.
I am on the fence as to whether to stay with a 1TB internal or switch to a 2TB? I read somewhere that upgrading the hard drive is not a D.Y.I. Is this true? That would be a major bummer.
If I want to upgrade to a 2TB later on, roughly how much would an the Apple store charge me and does it matter if the hard drive was not purchase through Apple?
My iPhoto Library is growing and I also want to run Windows. Can I store my iPhoto Library on and external instead on the primary drive? How disk space would I generally need to install Windows?
Is a 2TB more like to fail than a 1TB?

The ideal solution is at least one & better two backups of everything important to you. How you do that depends on what's important & how much file space it requires. Nobody but you can determine that, but for example I favor one Time Machine backup plus one clone of my internal drive (which contains everything I care about).
The two backups are not equivalent. Time Machine archives every unique file, including those I delete or change, so I can for instance retrieve an early copy of a document I created a month ago or a version of it with changes made a week later. However, it is not a startup volume -- its files must be transferred to a startup volume to use them. It is in effect a series of snapshots of the startup volume at different moments in time. Because of this, it should be much larger than the startup volume for best results, or set to exclude some folders if that isn't practical. For example, because I typically store 8 to 10 copies of DVD's I own on my iMac for immediate access, I keep them in a folder I exclude from the Time Machine backup, since if anything happens to the copies I can make new ones from the originals, which are safely stored away elsewhere.
The clone is an exact copy of what's on the drive at one moment in time, so it does not let me retrieve an early copy of a document I have since changed. However, since it is an exact copy of the startup drive, I can startup from it if something happens to the startup drive. I can also use it to test things like updates or questionable OS hacks without risking the normal startup drive.
This works for me; something else may be better for you, especially if you plan on filling the internal 2 TB drive to near its capacity with unique files. Again, bigger is better -- the more capacity you have for backups the more options you have.

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    com.apple.message.domain: com.apple.calendar.store.inconsistency
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    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
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    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:32:27.116 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:33:36.379 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:33:36.425 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:34:11.034 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:34:11.034 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
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    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:34:44.993 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:34:44.993 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:34:45.039 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:35:20.013 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:35:20.014 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:35:20.014 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:35:20.015 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:35:20.015 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES
    23/06/2013 00:35:20.062 CalendarAgent[195]: 
    com.apple.message.domain: com.apple.calendar.store.inconsistency
    com.apple.message.signature: Other CalDAV
    com.apple.message.signature2: etag (ctag)
    com.apple.message.summarize: YES

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