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Syncing / help cleaning up my messy virtual closet....

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ok, so this is kinda messy.
Basically this is several questions but any answers are better than none.
I have an iPhone, a google account, picasa, a windows 7 laptop, and an android Samsung galaxy note tablet, and an old webshots account (now Smile)

On those various devices, I have lots of photos, documents etc. that I would really like to keep. Problem is I have had this laptop for over 4 years now and need to wipe the OS to clean it up, the iPhone (two years accumulation) is going to need replacing sometime this year so I can go to a cheaper carrier, and the android is just awesome, and the webshots account is hard to sync so I don't add to it anymore, but I'd like to move stuff out of it to something else.
About a year ago I put Picasa on the laptop to try to start moving some of my data to cloud storage so that I can safely erase the laptop.
I do use photostream for the iPhone so that has a bunch of stuff in it too.
However, my dilemma is that I have so overcomplicated my life (well.... It was a complicated last two years so it's bound to show)that I can't figure out how to find anything anymore. Photos that were on my phone suddenly are not there anymore, then later I find them on my laptop in picasa, when I look at picasa on the web some of the stuff on my laptop isn't there, so how do I know what is safely in the cloud and what isn't?
Same for iCloud/Photostream. after upgrading to iOS 5 on my iPhone, I can't find half my stuff. not ALL of my stuff, only SOME of it is gone. which complicates things further.
Does anyone have a good housekeeping plan to point me in the right direction on how to get this mess straight so that I can find my stuff again?

Photos are my main problem right now. I have never really had a great system for those, and I moved a lot and went through a house fire at one point so I don't really have printed photos, everything is on these.
Other docs went to google drive or dropbox. those are my household and business filing cabinets, but I have too many photos to (cost effectively) use those for pictures.
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