Question regarding video software.

During the time the Doo Wop Society was in existence, we recorded our musical shows using a VHS camera recorder. Some years back I converted the tapes to DVDs; this was a straight dubbing without adding any chapters. I probably have close to 50 DVDs with each one about the usual two hours in duration. Additionally there was a similar organization in New Jersey that produced similar shows so I have a dozen or so DVDs (also converted from VHS) for this club too.

The DVDs have a combination of musical performances along with the introduction of each performer. I would like to copy these DVDs to a hard drive and edit them so I have chapter marks for each song; there may be about 30 songs on each disc so we could be talking about 1500 songs that would need to be separated by chapter. 

My plan is to have all the DVD performances copied to an external hard-drive that I would plug into my Xbox. With an Excel spreadsheet I could see the chapter number for a particular song or performer, and immediately go to that performance just like we do with store bought movie videos. If I can’t so this with the Xbox then I’d just have the videos on a laptop that I could connect to the TV.

I imagine I would have to copy the DVD to my computer first, and then add the chapter marks. I’ve done this before on a disc but have not tried this with a video file.

Is what I’m suggesting possible and is there a software that can handle this? 

Thanks in advance for any guidance you can provide.