Here's where I wound up:
BOOKS - look each title up on Amazon, sell the one's worth more than $5. Donate the rest to a local book store or charity. Sprinkle a few good titles around town where people will find them (gifting).
UPSIDE: books stay out of landfill, they go from the one who does not want it to the one who does, I earn back a few bucks off the books value.
DOWNSIDE: the time I spend on Amazon looking up each title is the same as time spent shopping. I'm still engaged fully in the world of stuff. My consciousness is not free until this part is over. The question is, is it worth it? The books are shipped all over creation. Yes, the fuel was already being consumed as trucks deliver mail anyway but volume surely has it's impact.
CLOTHES: sell a few great items off on ebay, gather most of it for the next local clothing swap, donate the least great stuff to local charity. I could compost some of the organic fibers but to be honest, I dont think there's much of them!
UPSIDE: I get a few bucks for stuff that was really expensive, my community gets a free splash of new to them clothes. Without question I've found that if I have tons of clothes I wear only a few things over and over. When I have less clothes, I wear everything and circulate through what I have better.
DOWNSIDE: Again I'm spending a bit too much time still engaged in the world of stuff, clothing donated to thrift shops winds up shipped to 3rd world countries where they are sold so cheaply that people stop buying locally made items and therefore people stop making local textiles and the knowledge is lost.
CONCLUSIONS: Buy waste (reuse/used items) when you can. Or don't consume it in the first place. Before buying anything new contemplate the burden it will be and how one day you'll have to figure out what to do with it. Remember that even getting rid of it consumes consciousness and takes one away from living.
If buying new, items that are of better quality, and do not expire or become obsolete are worth buying and spending more to buy because they can be resold back into the market and do not become landfill.
If you must buy stuff buy tools, they're not stuff... they're stuff that makes the stuff you dont throw away.
Similarly, handmade goods almost never go to landfill, they contain valuable emotional memory. In a sense they last the longest. Make more goods buy less goods.
Organic natural fibers can be composted. Consume these kinds of textiles and NO synthetics.
Image: a drawing I did a few years ago.