Well on the bright side, all of our NM collectibles should appreciate with each careless packing job

Seriously, I totally agree. Super frustrating to have to deal with preventable damage. I just lost a NM book to crappy packaging this week.

Consider that someone selling a larger lot instead of taking the time to sell individual items almost certainly doesn't have the same appreciation for the products as collectables that we as buyers do.

I've been buying on eBay for 19 years. The reality is, is that some sellers pack well and most don't.

I used to spend a lot of time messaging sellers to pack my stuff right, I've even sent boxes with packing to them. You can't do that anymore because they have a limited amount of time to ship out or they'll get their account dinged. I've offered extra money. I've done everything I could think of.
You also can't go by feedback or experience, most buyers have low expectations and know nothing about proper packaging. We are the oddballs and sellers on eBay or most anywhere else would rather have a customer with low expectations than one of us nitpickers. If you think about it, the money that they'll make on the item is pretty much the same - why deal with one of us if you don't have to.
Also, take a look at any category and see how many sellers call something that is pretty much ragged out, good or great condition. It's not always them upselling - they just really don't know. Good condition means it's not torn in half or had ever been on fire   That seller won't think a corner ding is significant.

I used to buy comics in a comic store. How many people make certain that they pick out a perfect condition book when they buy one. I was one of the few, and I was laughed at many times by the same people that knew what condition meant. They were laughing at me because I wanted all of my books in great condition - I didn't care if they did or didn't go up in value. Most of them saw that as a huge waste of time and effort, to them only books that were already valuable was there any need to be concerned about condition.

One thing I learned about buying online when I bought a lot of Antique Glass. I'd get great deals on eBay, or at least it seemed like it. I could go to local Glass Shows to buy a lot of the same stuff, but the Glass Show dealers have more overhead than an online seller so they charged more. I figured out for what I paid online, with pieces not being honestly described or broken in the mail, the time spent with returns and having to pay for shipping back, the time setting up Paypal claims. Buying one way was really about the same price as the other if I figured my time as having some kind of value.

A lot of things I can buy local, but so far not D&D stuff (the pre 1980 stuff that I want) if I could, even if it cost a lot more, I'd never buy this stuff on eBay.

One thing I've recently tried was joining a group on Facebook, an auction group for RPG collectors by RPG collectors. So far I'm 0-2 on packing, or 1-1 depending on how you look at it. Both packages were not packed well, but only one had the contents damaged in the mail. The one that came undamaged, it didn't come as described in the listing - just can't win.

Only piece of advice I could offer you - if you find an online seller that does a great job. Pay his or her price if you can, they are worth every penny.

In my experience, contacting the seller *before* you bid/BIN to ask how well they pack and to see if they're receptive to any shipping/packing requirements you have, is the best way to ensure you get the shipping experience that you want.  Essentially, you want to communicate that to you, the shipping experience is just as important as an accurate product description.

If they don't reply or seem resistant to requests (packing peanuts, bubble wrap, securing loose magazines in plastic and cardboard, etc...), then you'll be taking your chances with potential shoddy packaging.

Skullhammer wrote in Ebay experiences:In my experience, contacting the seller *before* you bid/BIN to ask how well they pack and to see if they're receptive to any shipping/packing requirements you have, is the best way to ensure you get the shipping experience that you want.  Essentially, you want to communicate that to you, the shipping experience is just as important as an accurate product description.

If they don't reply or seem resistant to requests (packing peanuts, bubble wrap, securing loose magazines in plastic and cardboard, etc...), then you'll be taking your chances with potential shoddy packaging.

I did that all the time in the early days and don't anymore unless they are new sellers or selling something that they never had before. It can be real hit or miss though. It's not NKG or the other sellers that typically sell this stuff, it's the inexperienced at selling ex-gamers and the experienced eBay sellers that don't typically sell this stuff but they found it at a garage sale or the like. I know that second group gets some condemnation on here but let me say this about them - they are the ones that are out there finding this stuff where collectors are not. I just helped a long time eBay seller identify and price about 60 items of 1E and 2E books and box sets that she picked up at a garage sale on the 3rd day. If you know Garage Sales. if she wasn't there to get them, they could have easily been thrown in the trash after the sale. The person having the garage sale was asking almost nothing for them.

Back to the messaging part - I'm a Reseller, not online though, but I'm in a group for them on FB. It's been a little eye-opening. Not all sellers but enough of them see what you are talking of doing as being a potential problem buyer - and they just block you right off. There are plenty of others on there that tell them they are stupid to do so - that they are losing their better customers that way, but they don't care. In a way they are right, if they are continually going to do a mediocre job - they can sell to dumb buyers all day long and never have a problem. The problem is that sometimes otherwise great sellers will get offended by that message because they've been doing this for years and then they'll be done with you or intentionally do a crappy job packing or whatever. You don't see it so much with this stuff because almost everything comes up occasionally, but there are things I want to buy that only show up every 7 years or so. There are things I've never seen for sale on eBay but I know they exist, more things than you'd think. After 20 years of looking for something that completes a set only to find out I burned that bridge with the seller because I insulted him with my question - it wouldn't be the end of the world but... I wouldn't have believed it until I joined a Reselling Group to see how common it is to get blocked or just toss your stuff in a box because they are mad at you. Plenty of sellers like to play the game that it's always the Post Office's fault that something gets damaged in the mail too. Sometimes they'll even help with that. Seems crazy, it is but it still happens.

One final thing, when you mention using bags and boards or peanuts. That is asking the seller to spend time and money to do so - it might be unexpected to them. They were expecting to put that book in a free polybag mailer and now you have them running all over the place and spending money. One of the online seller's greatest enemies is their unpayed for time. Like I said originally, I've payed for better packing or given them extra money to do a good job and it still isn't done right and the seller doesn't see it as their fault - they did it the way you said to, and to them it's on you, whether they really did it the way you asked or not. They can also be as accommodating as can be in those messages because they want you to bid, they may not really want you to win though - second highest bidder sets the price in an auction you know.
So only buy from experienced RPG sellers, it hasn't worked for me yet in that FB RPG Auction Group - they're supposed to all know what they are doing and I'm afraid if I complain, they'll kick me out. I'm the new guy there.

Thank you for replying Skullhammer and apologize if this is rant-y or off point.