burning bootlegs to HDD -- how is metadata set / maintained?

so i'm thinking of going PC / network, but have always been scared of having to rip not just my 3k store bought cds but also all my bootleg recordings. 

i get that at some point i'd need a keyboard interface to the ripping process in order to type in album name, artist, track name, etc. but a few ?s

1) is it easy to associate bootlegs with studio releases (which i gather any good ripping software would auto-capture)? ie all my live phish shows go with my phish studio releases? 

2) given #1, where i have to type in metadata for every bootleg, sure seems like i'd need a full PC at hand for the initial burning process (getting rip onto HDD. after that, i could ditch the PC and go NAS>streamer>Dac) --is this correct?

3) this is an explosion of data, and i gather the way to go would be NAS. --if i go NAS to house the data, then what would i need as the 'in between' piece before my dac? (yes, i've no freaking idea what i'm doing or what's out there). dont sweat budget, just trying to understand options. 

thanks all
I know how overwhelming this can be. I did it last year. However, it was worth it. 
You need a program to burn the CD's to your PC hard disk. I use JRiver, but there are other programs and I am sure others will post their ways.

I use my pc to play music from the hard drive.(I didn't go the NAS route) and use either a usb or SPDIF cable to the dac.
I have no experience with bootlegs. Hopefully, others will chime in.