I would like suggestions/help on three topics with regard to building a Personal Digital Memory Palace:
1) Streamlining its creation
2) Organization of it
3) Backing it up
If anyone has any suggestions, general or specific, and/or can point me to useful resources or others who have done similar things, please let me know.
Please read on for details...

I'm preparing to move for grad school in August 2006 (very likely across the country). I've realized I have an inordinate amount of crap; this is bad for moving, but also bad because many things that have nostalgic/sentimental value, or information/entertainment value, are presently not easily accessible because they are physically scattered or tucked away somewhere.

So to help with the move and to help consolidate all the things in my immediate environment that are significant to my life, I have decided to go all out and put as much of it into my computer as possible, discarding as many physical originals as I can. Thus, I have set out to build a Personal Digital Memory Palace. (got the term from Bruce Sterling's novel, "Holy Fire," where its meaning is pretty much the opposite of how it was used by Jesuit priest Matteo Ricci in the 13th century)

Achieving this will likely provide great benefits, both foreseen and unforeseen; but I have to get there first.

My computer is an Apple G5 dual 2.3gz with 2gb RAM and a 400gb internal hard drive. It currently runs Mac OS X 10.4.3.

Here is my present plan for each category of things to be included in the memory palace:

Anything flat (photos, drawings, flyers, letters, etc.): will be scanned in (at the highest resolution I can manage to sit around waiting for, maybe 500dpi? suggestions?), and then discarded.

Physical objects that aren't flat, aren't inherently valuable, but have value in terms of memories: most will be photographed (using an 8 megapixel digital SLR; suggestions?), and then discarded.

My entire CD library: will be ripped (I'm thinking mp3s at 192 kbits/s for a balance of high [not perfect] quality, high compatibility, and reasonable file size [files don't need to be tiny, but they can't be huge]; other suggestions?), and then at the very least collapsed into a no-jewel-case notebook archive.

CD-ROMs & floppy disks: will be ripped (for disks that I made that simply contain files, it should be enough to just copy files to the hard drive, but for anything that's an installer or, say, required to run a game, I guess have to make disk images, and may even have trouble doing that with some; suggestions?), and then floppies will be discarded and CD-ROMs will be saved in a notebook archive if they are ones that wouldn't function the same from a disk image format or a 2nd-generation burned CD.

Audio cassette tapes (yeah I have a few): anything available on CD will be discarded outright, but a few may have to be ripped (I'll likely use Sound Studio by Felt Tip Software; suggestions?).

DVDs: fortunately I don't have too many, but it would still be good to rip these and archive the originals in a notebook. Two potential problems: I'm not sure how to do that (I've heard Roxio Popcorn maybe?), and the files would be large. Suggestions?

VHS tapes: anything that's available on DVD will be discarded outright, unless it has other value (e.g. autographed), because I can always just buy the DVD and rip that into the computer. There are a few VHS tapes not available on DVD (some b-movies, some home movies), and I would like to rip these, but I don't think I have the capability. Any suggestions on cheap ways to do this?

Books: bahh. This is the toughest one. I like keeping around a lot of books I have already read and am not likely to read again soon (from scifi paperbacks to textbooks). They are heavy and take up space, but I love them. I am already making a text file that's a history of books I've read (and this could be annotated with thoughts/memories). I suppose I could scan or photograph covers, but I'm certainly not going to scan contents, and most books aren't available as electronic text yet, not to even mention ones with illustrations.
I'm of a mind to just cart the whole huge heavy lot of them with me, but that's no long term solution. Suggestions?

Webpages: I have a lot of bookmarks, some of which are organized by category. I have just started using del.icio.us, which seems useful. But I don't retain control over any of that web content. If some webpage goes down, it's gone to me (unless maybe it's on archive.org, but still). So would like to download as many of my bookmarks as possible, but I'm not sue how to go about doing it. A few times I have used Safari's "save as webarchive" function, but I don't know pros/cons of that or other methods, and would like to keep downloaded content as organized and accessible as online content. Plus, what if it's an entire website I'm interested in, or something in flash? Are there tools for doing this kind of thing? Suggestions?

Have I overlooked any major category that could be included?

In addition to any suggestions on the above methods/categories, I would very much like feedback on the following three topics:

1) STREAMLINING the creation
Many of the above processes will take a lot of time and effort. I am very interested in streamlining things. Are there time-saving methods? Anything that can be automated? For example, maybe a program/applescript that automatically rips a CD on insert or creates a disk image of a CD/floppy? I am generally competent with most tech and with programming, but am not an expert. Also, maybe there are some tasks that can be affordably outsourced? Like maybe paying a person/company to rip VHS tapes for me, or to scan a bunch of stuff. But then how would they label/categorize those items without my personal knowledge of them? Perhaps it would still save time to just do that myself later?

2) ORGANIZING
All of the above only covers getting everything IN to the computer. I will also have to make sure it's all organized and accessible. If some image file is buried and forgotten in a backwater folder on my hard drive, is that any better than the original photo sitting in a shoebox under the couch?

Something that seems useful is the ability to have robust metadata for each item, so that it can be sorted or searched for by, say, several different tags (e.g. "funny" "college" "family" "from my friend Such-and-so"), by chronology (e.g. "1996" "sophomore year in high school"), as well as by standard things like file type or whatever. Annotation is a must (e.g. "This was a photo taken on our first trip to San Francisco. A bird almost crapped on me right after this!" or "I got this bottle opener keychain for free at a concert and even though it was a piece of crap I used it to open many beers with my old roommate Such-and-so."). It would also be great to make links/relationships between items. There could be a cluster of items from the same context/event, or a cluster that are related semantically. Of course, all of the metadata stuff is in direct conflict with the first goal of streamlining, as I'd have to thoughtfully enter a bunch of stuff by hand for each item. But maybe I just do that later, after it's all in the computer? But it'll probably be easier to do as I'm entering items, especially if the originals are discarded. Too bad I can't clone myself a bunch and do a wiki. Suggestions?

All of the stuff will have to be browsable. I don't think the Finder will cut it. What software tools are available? Maybe no one tool, but a combination of a few?

3) BACKING UP
This whole enterprise is lunacy without a serious backup scheme.
Right now I have a dedicated external firewire hard drive (Lacie 200gb) and am using Data Backup from Prosoft Engineering to make weekly compressed backups of almost everything on my computer's hard drive onto the external one. I also have an Applescript that backs up my usb memory stick onto the same external HD every time the stick is plugged in (triggered by the fantastic little program Do Something When). I will soon be getting a 600gb backup external HD, as I will need more space and will likely be throwing a laptop into the mix before long.
Are there better ways? For instance, better tools, better schedule? Other things to consider (e.g. power surges [it's all plugged into one of those huge 16-plug powerstrips right now], data corruption, versioned backups)?

But my real concern is this: an external hard drive with a current backup will protect me from my computer's hard drive failing, but what if the building burns down while I'm away? I'm screwed. Doubly so after discarding many originals. So: what options exist for offsite personal backups?

Keep in mind, we're talking about maybe 600gb here. So something like .Mac/iDisk won't cut it.

Are there companies that offer large personal offsite backup services? I'm guessing that would be expensive though? I am of pretty meager financial means, and will continue to be so as a grad student, but then this would be something very important that I would be willing to spend for.

Maybe I can keep a 2nd backup hard drive on the campus of whatever university I go to and have my computer VPN into it to make secondary backups. Maybe that could even be done at another location like a close friend or family member's house. But wouldn't that be slow? And require the HD to be hooked up to a computer there? I would then have to also worry about security, which I haven't even been thinking of (my computer has current firewall software and is only physically accessible by my girlfriend, who I trust).

Maybe there's an alternative to dedicated hard drives? If I have a laptop with a lot of space, I can backup to that and then at least I'm taking it around with me so it's not always in the same place as the main computer? I shudder to think about burning a bunch of backup DVDs (or whatever); the process should be automatic, and DVDs would still have the problem of being in the same location as the main computer, unless I was mailing them somewhere.

Hm, I know that was a lot. Any input would be greatly appreciated. Thanks,
~jason