Tippy, are you there? Don’t be shy. I alway think it’s better and nicer for OPs to participate and not just lurk or disappear after asking for and receiving a bunch of friendly advice and questions.... My two cents is that the urge to simplify/renew and maximize $$$ are in conflict. In particular spending time trying to get money for used CDs is a huge waste of time IMO, given that only an extremely tiny quotient of rare CDs command decent prices. Books are even more sadly not in demand and hard to sell. Vinyl can offer a better return on the effort of selling but only if the stuff is in super clean condition. Quickly get a savvy take on whether you’ve got albums that are worth anything. Then strike quickly, donate or give away the dross, and don’t spend time getting bogged down in this process if you’re looking for a fresh start. Get rid of it fast and don’t look back. I agree you may live to regret the whole thing, particularly if you toss overboard albums that you love and mean a lot to you.