However, plenty of people really only open their wallets to official dead tree publications by WotC, thinking that's the only kind of product quality tested enough. The only way you'll ever get their money is to hand them impressive stuff for free first.
I'm mostly in this group. For some reason that is very real to my psychology, but which I haven't analyzed, I just am not very interested in 3rd party D&D. Part of it is probably that I want my D&D to be actual, product identity D&D multiverse situated material. Now that DMs Guild exists, that is actually possible, so barrier down.
The other part is definitely about quality testing and product congruence. I usually find that the free third party products I've looked at (and I've never to my knowledge downloaded any PWYW D&D, and definitely not from the DMs Guild, so I mean actually free rather than PWYW) aren't
like official products. I can look at them and say, "that's not how it would be done as an official product", "that isn't 5e philosophy," etc. If you want to sell me another game -
sell me another game! I love non-D&D games! But don't give me your own interpretation of D&D, because I have
my own interpretation and am not really interested in buying someone else's. There are some exceptions I've seen, where the designers of the product really did
get it, and those are pretty cool, but by and large that's not been my experience.
What else do I not want? Something WotC might do themselves in the future. So I won't pay for monster conversions and such. I really, really want a certain subset of monsters converted, but I want the official versions of them.
To get me to buy something from DM's Guild, it would probably require a free preview of some sort to see if I like the philosophy it is designed with. It would have to have content that did something WotC isn't going to do, but that fits with the kinds of stuff they would do. It has to feel very D&Dish to me, not like someone's house rules. And I have to feel like I'm getting enough to make it worth it. I'd rather pay $6 for a larger product I can get a lot of use out of it, than $1 each for five shorter products that aren't big enough to interest me, even if the total page count comes out to be the same (unless the smaller ones are
really, really good and relevant to my needs).
Yeah, I know, now is where I have to produce actual examples of what I'm talking about. One example might be adventures. TSR-era
Dungeon magazine style adventures. While they were produced by a variety of authors, you knew there was going to be world consistency, content boundaries, and some unwritten
rules that TSR used to decide what to allow--above and beyond quality. The adventure isn't going kill off known D&D characters, it isn't going to violate cosmological or other world assumptions, etc. It's something I can more or less drop into my game without fear of it messing anything up. You don't have anyone enforcing that at DM's Guild, so I have to have evidence that's what I'm going to get, either because I'm familiar with those producing the content and I know they have that philosophy, or because it's highly rated, they tell me their philosophy, and/or they hand out a short adventure as a free preview for a book with multiple adventures in it. And I must restate that this is only really possible now that DMs Guild exists so that full D&D IP (at least as long as it doesn't stray into non-FR settings) is available.
Another one would be a brand new, well-developed campaign setting (in the D&D multiverse) with a theme that interests me, and with
excellent reviews. Lots of people have made settings though, and it's pretty hard to get one so high up there that everyone wants it. But if it happened, it might make my list.
A third one (and this is real iffy, but I have an actual example) might be some high-quality, simple rules revisions. For instance, the Way of Four Elements Remastered is excellent. I don't normally go for someone else's house rules, but the crowd-sourced work on this one created something pretty awesome that feels like it could have come out of an official "Complete Book of Monks" or some such. Of course, they can't sell it on DM's Guild because it was already released freely elsewhere, but if someone were able to put together that sort of thing, I'd occasionally see a few of them that might be awesome enough for me to want.
Yeah, I'm a really tough sale, so I shouldn't be used as the standard audience assumption. But I thought I'd weigh in as one of those people who is extremely unwilling to buy any non-official D&D stuff on how you can sell something to me.
I've downloaded a good handful of PWYW for free and reviewed several. One I used in a game and that one I went back and threw in a dollar for. I'll be looking for more by the author now that I know it both read and played well.
Yep. I've only downloaded a few PWYW products (none of them D&D as far as I recall), because I don't consider it synonymous with free, even though I haven't yet paid for any of them. Generally, I'm going to pay for it if I use it. And since that is already on my mind, I'm not likely to download (even for free) unless I think there is a reasonable chance I am going to use it. If I do download it, I'm generally going to download it free initially, evaluate it, and then either pay for it and use it or delete it.