The other thing I'm interested in, and wonder if you have thoughts on: When you pass, your personal library is inherited. Will people know what to do with your digital library? Will it be useful? Will people want it?
The tools for processing PDFs into searchable text have a lot of warts. For a while IBM was offering a free Watson service to do this (now its part of Watson Discovery) which has some warts. I did manage a set of perl scripts that would post process the statements that I downloaded from the bank into CSV files, but I would still like to pull tabular data out of PDF book scans to make the data they provide more useful.
I have a simple frontend based on the perl Mojolicious module which Blekko had developed as part of another project but my indexing tools are still quite primitive. Simple bi-gram and tri-grams, and a growing synonym index. I don't give it enough queries to use my own traffic for ranking feedback. So basically everything is nearly equal rank. Basically I am about to the AltaVista level of search capability :-).
The vision is it just runs as a server and anyone on the same network can access it like a web service an pull up documents (and in the future media) of interest.
I ended up replacing my NetApp StorVault (6TB (4TB usable), RAID6) with a FreeNAS box from iXSystems (24TB (20TB usable), RAID6) which cost me a bit more than $2500. (it is also much quieter than the StorVault was :-)). And on that 20TB I've stored a bit more than 200 book volumes that I had digitized at 1DollarScan, probably close to 1000 magazines (scanned generally manually with my ScanSnap 1500), and perhaps as many PDF documents that were never printed to begin with (like data sheets). I also have my music collection, and I have recently looked at putting movies on there as well since the streaming services are letting me down here as well.
At the end of the day it is the 21st century version of one's personal library.