1. Does anyone know a social media marketing person that actually enjoys doing it and is in the D&D knowhow that wouldn't mind talking to me and giving me some tips or possibly for hire?
After the fact, but SEO and social-media buys (ie Facebook ad impressions and Google Adsense) are basically your main social marketing tools if you are looking beyond using influencers. That being said, your biggest tool to leverage are unfortunately the influencers, especially within the niche hobbyist sphere that is 3rd-party adventure module writing.
2. What do you do when you have to advertise but hate social media and just want to be a hermit and write/publish adventures and once in awhile hop on forums and argue about paladins and shit? Any thoughts? Is there any hope?
Well, you can throw money at it (buying online ads), but honestly, the indie RPG industry thrives on connections and recommendations from established individuals who already have their own social media audience, and those are the people you need to have shilling for you in order to gain any kind of traction. If you can't connect with any of them, then you're left to build your own audience in the same way they have, only their audience was not borne of product but rather blog-style advice (they didn't put out the products that made them well-known; they became well-known and then put out products). If you build up a persona as a knowledgeable authority in the world of D&D adventure writing, you'll slowly build a following who will hopefully buy your products.
3. Like, how did Shadowdark do so amazing? I never heard of it until it blew up Kickstarter--so I didnt see the social media or advertising tricks or anything like that to learn from---seriously where was the advertising?. I honestly don't want to be THAT successful...I just don't want to keep stressing on if a kickstarter is going to fund or not so I can pay myself back for most of the art. Breaking even would be great!! And also--why don't these people write a book about how they did it? And if there is a book out there, can someone show me it--and something relatable to our hobby? It would also be cool if a certain reviewer wrote a book on adventure design too *cough* but perhaps that's another day's discussion.
The OSR scene loves to distance themselves from the mainstream D&D crowd, but honestly, it's their biggest market (just based on sheer numbers alone, even if most won't buy OSR products, the percentage of the mainstream audience who would buy your product is likely larger than the already-converted OSR audience in total). Newbies entering the hobby are some of the biggest spenders, easily willing to drop hundreds (if not thousands) of dollars on the game. I don't know exactly what Kelsey or the others did (other than being a mildly-attractive woman), but I imagine they didn't shy away from mainstream audiences, and probably got a few shout-outs from influencers on that side of the fence to bolster their sales (all the GinnyDs and Matt Colevilles of the world, and their ilk).
4. I've tried other reviewers that are mostly on youtube or whatever, like what's his name and that other questing dude, but I send stuff and maybe it ends in the trash, I don't know. Honestly, my main reason was to get another few opinions so I can improve in design rather than a method to get the word out.
In Marketing, there's something called a "USP" or "Unique Selling Point" which every advertising campaign revolves around. Essentially, it is the thing that sets your product apart in a sea of sameness; the reason people are going to buy your adventure and not one of the thousands of other ones. Effective advertising revolves around a solid USP. If you cannot identify one in your own product, it's a big problem; it means people are going to skip your product for similar ones at a better price. In the same vein, anyone you try to impress with your product will be looking for a USP. So ask yourself this: What is your USP, and why should the people you send your product to care about it? Why is it worth their time and effort to plug on your behalf? If you don't have an answer, then that's why you haven't been getting the desired effect in trying to form your partnerships - you haven't been making them go "wow, I gotta tell people about this!", and the only way around that is by either paying them to plug your stuff, or by being personal friends with them so they sing your praises as a favor.
5. This is the second place I've "advertised" (although I did it a little differently at the other place, lol) and I know I have to hit it and feel like a schmuck and go through all the BS fakeness, but I'm seriously open to ideas and I think it would help others. I realize some ideas take time (like 'building a community'....) but is there any hope for myself and other 3rd party small publishers when it comes to advertising for a Kickstarter, especially those of us who hate social media? I feel like all the advice on the KS page doesn't really relate to our hobby much, but maybe I'm wrong and if that's the case, can I get your email so I can send you a weekly newsletter? *rolls eyes*
This place is a tiny audience (probably a dozen active users), and most of us already have dozens (if not hundreds) of adventure modules in our libraries. If anything, we are probably even less likely to purchase since we already have so much. The wider audience is out there. The way to reach them is on the sites they visit, the places where the niche of the OSR touches the mainstream - YouTube, Facebook, Reddit, etc. Tiny niche blogs and forums like these may get you a couple solid sales, but you cannot build bulk unless you reach into literally dozens of similar communities; it's far more efficient to reach a bigger audience, even if most of that audience isn't interested in what you're saying. A small fraction of a huge pool is still bigger than a huge fraction of a small pool. As before, the successful creators have already dipped into the audience before releasing a product - just throwing your piece into the void isn't going to be enough. Also, don't be fake; believe in your product, and sell it like you believe in it - you see its worth, now make us see its worth.