Hi, It is time. Small by others, but I want to start moving my 4700 titles to digital.
I am committed to lossless conversion. I need a lot of priming on this, as I have generally ignored.
Hardware wise - I will leave for another post. I am not too concerned. I get the overall gist. Computer (with storage) > DAC > receiver (I have been reading up on this a bit, but it is somewhat secondary at this moment). I do intend to make a very robust storage solution with a serious cloud based back (this will be were the IT background will come in very handy).

What I am looking into at this time is really the software. From what I read, it appears that I can start ripping and organizing the music is a structure with minimum concern of the final library software. I am curious how accurate that is, and how deep the folder structure can go (or if some of the folder structure can be substituted with tags (more on this in a second).

Using the Dead as an example, I see a folder structure like this.

%Genre% > Grateful Dead > (Branches of to two sub directories: Studio | Live )
Picking up on Live
%Genre% > Grateful Dead > Live > 60s (70s | 80s | 90s) > Road Trips (Dicks Picks | Boxes | Dave's Picks | one offs)
(I may swap above, ie type of series, then breakdown years)

Am I out of my head, or would some of this granularity be better served with tags?
Meaning I may want to hear just 60s (or just 72 (ouch! More folders).

Then when it comes to Dead I may do some shuffling, but I would want to keep complete segues (Fire > Scarlett) - am I transferring these to digital as one file? Maybe a complete set (I am thinking some sort of tag here).

I am using the Dead as is will be perhaps the most complicated for my collection.

Next - as far as tags, are we limited to what available on the file properties (I work in IT but am more servers and infrastructure)?
I understand that more tags can impact performance - do to db indexing etc (maybe I go with a sql server backend.)
But I can see beside obvious of artists, album, genre (sub genre) , items above, personal ratings, I am also thinking of items such as user preference (meaning my fiancé will say play my music, and while she likes a lot of my stuff I want to tag that as Fiance)

I was looking briefly at subsonic and some others, and I plan to play around with a few before I get settled, but I want to get the storage and structure going, but not sure if that is putting the cart before the horse or...?

I am also leaning towards staying on the Windows platform.

Any thoughts would be greatly appreciated.