where do i begin?

The LPs would have to be digitized in real time. I'd figure an hour each, what with cueing, turning over, etc., so that's a big undertaking. I have not nor do I plan on digitizing my 300 or so LPs. The CDs can be ripped to a server more quickly, say 5-10 minutes each. Much easier to do if you can set up your server somewhere near where you do something else. I have a home office, so on days when I'm writing reports or doing billing, I can slip one into the optical drive on my server, start up dBpoweramp and then leave it to itself until it ejects.

The hardware is another matter, but if you're not up to dealing w the software, why even go there. If you are, you can start reading up on computeraudiophile.com, ask some questions, or find a vendor who matches up w your level of expertise/ignorance of the digital world.

One of the big surprises is the streaming world of Pandora, spotify, tidal, and internet radio stations. Tons of music to explore,

It is also possible to find online files of your vinyl albums where someone else has already done the digitizing for you. I would investigate this first to see what is available to you. Digitizing 1,000+ LPs is no small task and will probably take you a year or two to accomplish...