In another angle, it is the plus and the minus. How much you can keep that makes you happy? That must be realistically answered based on your own experience and history.
and how much else that you don't want to keep or cannot keep, that you can sell or give away in the allocated amount of time.
A 3rd aspect would be what else would you do if you don't go either path or go down one of the path.
Give it a margin of error and comfort, and the decision is based on the net.
I would not totally get rid of my stuffs, but I can choose to trim them down alot as needed.
and how much else that you don't want to keep or cannot keep, that you can sell or give away in the allocated amount of time.
A 3rd aspect would be what else would you do if you don't go either path or go down one of the path.
Give it a margin of error and comfort, and the decision is based on the net.
I would not totally get rid of my stuffs, but I can choose to trim them down alot as needed.
I can always sell a mill . Vertical saws and drill presses , grinders don't take up much room . That horizontal saw is a biggin and will eat up some space . 
I'm going to tag everything tomorrow and make them an offer they can't refuse , or it will be considered refuse to them . ( little play on words there )