Start by getting rid of all three Richard Simmons copies! Seriously. And anything else that you feel isn't worth looking at, let alone listening too, and save your listening time to things that you are, or may be, interested in. Life's too short to hang on to crap and there is plenty of crap out there in shellac and vinyl land. What others have collected in their lifetime may have no relevance in yours and you need to let it go.
While up here on the soapbox I'll also say DON'T record anything to MP3 if you value good sound at all. Nothing will put you off of listening to things you really like quicker than compressed lossy files such as MP3. Life's too short to listen to crap, too. Spend your time listening to vinyl rather than digitizing it.
While stretching this morning (no Richard Simmons albums in this house) I listened to the Schumann Piano Concerto on the EMI label and then, for the sake of diversity, Parliament's Motor Booty Affair, both on vinyl. Not as convenient as having it digitized but both sounded awesome and enhanced the start of my day. Plus, looking at the artwork on the Parliament album made me smile with its '70's goofiness.
Don't get me wrong, if you choose to MP3 all of your collection I won't hold it against you. But if you really like having mementos of some of your family's history hang on to the stuff you like and with the older stuff, like the cylinders, consider donating some of it to a local museum that would appreciate it. Get rid of the dreck - most thrift stores like Goodwill will take it off your hands and you will have lightened your load.
Happy Listening!