Designing content as a third party publisher for Paizo is not hard. You just go to their site, download the required material, fill out a few forms, send them in, and you can even be featured on the Paizo store. If you have the talent (and make no mistake, making fun stuff is a talent. It goes beyond sheer number sperging) you can turn out a new product every month or two months, or hell, even in a week or two if you're really fired up.
The Pathfinder SRD (System Reference Document) is online, and the Wiki is very handy to use. He doesn't need any of the books in print, and the books slow you down when you're working on something to sell. The only thing that might slow him down is statblocks, but with practice, you can whip one out in five minutes, set it aside, check your math and sources an hour or so later to get a fresh look at it.
He's supposedly got a name in the Pathfinder circles. Even if it's a small name, you still have people that would go: "Oh, yeah, this dude worked on that book I like, I should check out his other stuff!" and you could pick up a purchase right there.
It's not hard to sign up for RPGNow and DriveThru RPG. They've even got ad packages you can request that they'll pull the cost from your little supplement or whatever. (Well, I've got that option, not sure if everyone does) Yeah, they take 30%-40% (Again, I'm grand-fathered, so they only take 20%) but that's because they handle distribution, refunds, the credit card/PayPal processing, all that good shit. You just slam it up, advertise it, and BOOM! Sales.
GIMP is out there for your graphical needs and it's free. It takes a few hours to learn and is pretty good.
Open Office is a free one too.
Now, if he wants to get REALLY technical, he can go on the Adobe site and download like... I think it's CS2 for free. That works really well if you're running a 2004 potato. You can also teach yourself to use the Adobe suite for when you've got some money coming in and can afford a license. (I use CS5 myself).
With the Adobe suite, he can even do custom layouts with InDesign (My preferred method) and even build templates so his later stuff is easier to use.
Making maps isn't even that hard. A scanner is easy to get. HEll, $40 and you get a cheap printer/scanner. Hook it up, scan your hand-drawn maps. You make them with graph paper, and proper drafting tools ($6 from Wal-Mart) or just use GIMP/Photoshop with a grid (There's even a tutorial on how to make a grid on a layer that will print) and snap to grid, and you can make perfectly acceptable maps. Hell, if you print them in Blue you can claim your doing them "old school" and go get a style sheet off of Google Search so you have the ladders, traps, secret door parts to drop into your map. If you pass the savings on not using high end mapping software like Campaign Cartographer to the consumer, they don't mind the old "Blue Print" maps.
He builds a statblock template in Open Office that he can quickly plug numbers into, gets his mapping grid set up, open the PFSRD on a browser, and he can start going to work.
That's if he wants to do adventures.
Sourcebooks, like "The Secret Life of Gnomes" sell if you've got a good hook. Hell, sourcebooks are amazing sellers. He could do "Gnomish Raiders of the Iron Steppes" and people will at least look at the free sample, and as long as he isn't lazy and shows only the inside four splash pages which just contain bullshit and actually shows some content, people might be intrigued enough to pick it up.
So he's got the resources, a name, and a distribution platform. What's stopping him from building a brand?
He can't say "artwork" because, to be honest (and I've tested this), you can throw up a book with a minimalistic cover and no interior artwork and it still sells if you pass the savings on to the customer. Hell, I tested it with hand drawn (ruler, french curve, compass, graph paper) maps, and told the consumer: "This is bare budget, that's why it costs you $4.99 instead of $9.99 for this. Enjoy!" and the feedback I got is that they liked it. There's plenty of Public Domain artwork out there that is VERY nice that can be used for covers and interior art and the like if you take the time to look. A little processing in GIMP (a free program, SGG) and you can make it fit right in.
I mean, he'll have to get used to embedding hyperlinks in the document, having an easy to use ToC, and the like, but it's not that hard.
Open Office, GIMP, some elementary school art supplies, a calculator, and an Adobe PDF converter and he's set.
He's got the time. I mean, back a long time ago on a drunken bet, me and a friend made a supplement (Charge a buck for it) in less than 48 hours, from concept to upload. It sold a shitload of copies and everyone who bought it liked it, even though the inside cover proudly proclaimed "WE'RE FUCKING DRUNK!"
Building a brand isn't hard. You start putting out good supplements/adventures/sourcebooks and have roughly similar covers and contents, your own writing style, and good solid stat-blocks with well balanced crunch, and you WILL get a following. Once you build that brand, you're good.
He can't fall back on "I don't want TERF's to know who I am" since you just slap your made-up company name on it and be good. And yes, people will buy supplements from XxXWeedLord420XxX on the cover if everything's solid.
Everyone knows game designers are weirdos, so he can't fall back on "I'm a recluse!" Paizo isn't going to out who he really is, and he already works with them anyway. Hell, he's probably got more industry contacts than I do.
He can't claim "Oh, my enemies..." because unless his enemies work for Paizo and can send him a cease & desist or unless he's somehow pissed off PayPal or RPGNow, they don't care about shit but the money.
He can't claim "Oh, I don't have time..." because the amount of time he spends sperging on Twitter could be used for flavor text, crunch, or exposition/explination text.
He HAS the ability to make money. He has the ability to start bringing in a decent income.
No, it won't happen with the first one or two books he puts out, unless he catches lightning in a bottle. But if he builds up a good catelogue, people notice that shit and become curious. He gets 10-15 supplements (easily doable in 3-6 months if he puts the effort toward his projects as he does toward Twitter) out on his store page, and people notice, people start buying, and if they like his stuff, he's got a catelogue for people to purchase from.
He brags about writing articles and the like, but unless they're paying him 5 cents a word, he'd be better off putting that in his own splat-books.
And once he gets a good catalogue, and people see he's a solid performer with good solid work and capable of putting out steady work, he'll start getting invites from other publications to write a guest spot for them, which gets his name out further. (THAT'S when exposure bucks spend)
When he gets a good enough following, he'll have young and hungry artists coming to him, saying "Hey, I'd love to be in Secret Gnome Girls VII! Check out my art!" and he can pay them bottom rates (NEVER get them for free. Jake, I know you're reading this. Always pay at least a pittance for them. Hell, I once paid a crate of Mac & Cheese, some Top Ramen, and $25 in Spam on my credit card for a full color insert because the artist was hungry and hadn't eaten in 2 days. I'll bet he'd do a color insert for me on credit because I was there when he was hungry and people don't forget that. Ever) for good artwork, paying them more for the second and beyond books if they prove popular artists.
Once he starts getting in money, he puts half of it back into a kitty to buy artwork, upgrade his software, hire an editor, and other business expenses, and keeps the other half for himself (Or uses 25% to pay off people he got artwork from on credit).
If he's got this talent to keep getting work with fucking PAIZO, has all this free time, and he has all these industry contacts...
Go third party publisher.
Tighten his belt for a few months and learn how to make the 12 Essential Top Ramen Recipes, drink water, and be a starving fucking writer till he's got a good catalogue and build a fan base.
And never beg again.
If a drunken retard can do it, so can he.
