First thing I'd do while you're considering your plan is take your camera and walk round your house videoing everything, opening all cpds/draws. Then copy the video to a location that isn't your house (e.g. upload to cloud or physical copy at work). 15 mins work. Several short videos may be easier to upload! The video can be used to jog your memory about what you own if you end up with a total loss e.g. house fire and the insurance company expects you to list everything you owned.
As far as cataloging possessions I use Evernote. I have top folder House, Sub-folders by Room, then a Note for each item. I like I can stick the name of the item, a photo, the manual, the receipt (email or a photo), and value information all in the same place. It's automatically is backed up online. Takes a while though - mine is still a work in progress. I'd start with the valuable stuff/stuff most likely to get stolen (electronics/tools/bikes). I can move the Note between folders if e.g. it goes up the loft. There's generally little point in cataloging low value or transient items.
I don't track overall contents value as not needed in the UK.
Eljay