I have almost 400 trades and probably 99% of them have been PWE. I prefer to make/send smaller trades, max of 15 cards. (The majority of all the cards I send and trade are usually less than the cost of sending a bubble mailer.) No one I've traded with has ever told me an envelope or cards have arrived damaged or with postage due. 3 cards or more go in a number 10 (long) envelope. The cards are placed in a single row of a cut 9 pocket page, unless it's 12-15 cards then I use 2 strips, folded over. The strip is placed in a thin cardboard sleeve. I use file folders, soda packs, Kleenex boxes but mostly cut down PO priority mail envelopes. I cut the bottom 1"-1 1/2" off used #10 envelopes that I receive and use them as a top cover strip over the sleeve. That also gives me a surface to write a note and the ID number of the trade. Depending on the cards I can mail up to 10 cards for a 70 cent stamp. 12+ usually require another 15 cent / additional ounce stamp. I have a small food scale that I use to double check weight and it seems to work fine. I then use clear shipping tape folded over the ends and a small strip folded in the middle of the top and bottom. I do this because I've had quite a few envelopes, mostly purchases from SportLots, that have arrived ripped and the cards almost falling out. DO NOT tape over the stamp! Put the stamp on top of any tape that is folded over the end.
Trades of 1 or 2 cards go in thank you cards, Christmas cards, birthday cards etc. I place those in a semi rigid sleeve and sometimes place an extra layer of card in the envelope also.
As someone else mentioned, and as I've been told at the PO, everything (PWE) goes through the machine.
As also mentioned, communicate how you want to send the cards. When I send a trade proposal I usually start with: "Hi, Interested in a PWE trade?"
The envelopes that I've received in damaged condition were ones where cards were put in a top loader and couldn't bend enough through the machine. There has to be some flex there and the multi card top loaders don't bend.
I have received trades in the rigid photo mailers. They seem to work very well, I'm just too cheap to buy any. A box of 80 #10 envelopes I think was $1.75 the last time I got one.
Finally, I'll repeat I've never been told that my envelopes have caused problems. I certainly hope they've arrived safe and sound for everyone I've traded with.
If you have any questions shoot me a PM and I'd be happy to try and answer them.