Choosing the right equipment

I think looking at used is definitely the way to go. Perhaps an integrated amp from NAD,Cambridge Audio,or Marantz with a MM phono stage built in. There are a ton of lower priced speakers on the market,Elac,PSB,Paradigm,just for an example. Turntables,ProJect makes some decent lower price offerings. There are more. Some folks might recommend vintage,which is fine. But remember,eventually old stuff wears out. 
 

      It’s wonderful thing you and your sister are doing for your dad. Kudos to you! 

We were hoping we could put something together for like a thousand or less. Just so he could listen to his favorite albums again in the mean time while we save to help him get his dream system. I know that's a tall order but we are trying our best!

Sorry, man with 72 Viking, traipse and high end circus performer wife not into budget gear but make good point. Take your $1k budget, divide between turntable and integrated amp with built-in phono stage, with maybe a little left over for speaker cables. I would stick to new. Most $500 turntables will be very similar in performance, so don't sweat it. Focus on finding a good integrated amp with phono stage. This will be fine to fill in, and leave room for things like speaker cables for him to add later as he is able.

These will get you done...

https://www.musicdirect.com/music-hall-mmf-13-turntable

https://www.psaudio.com/products/sprout100-integrated-amplifier/