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I realize that I'm essentially going to self publish my own RPG, so I can't rely on a studio to make my book pretty.

I'm going to have to pay people to do that.

How much art should I expect to put into an RPG rulebook?

And how much should I expect to pay?

That varies a lot by the artist you use. If you find a local artist at the community college who needs to build a porfolio and do X amount of internship hours to graduate..... it can be inexpensive. If you are hiring a well-known cover artist like Guissippe Rava (sp) it will be considerably more.

Some things to consider though. Yours is a historical based book, so there are a lot of photographs and public domain pictures from the government that can be used to fill it out. Those are free! There are also sources like Wikimedia Commons, Pixabay, etc. for free use artwork and pictures.

However, keep in mind if you can combine public domain images and some decent lay-out software (such as Canva or the like) you can probably build your own cover from Public Domain and software assets. However, such software is (usually) not free citizen.

Realistically, you will probably need 1 good cover, and maybe 5-10 full or half-page pieces of art after that. Line work is cheaper than full-color. I would save the full-color hi-res work for the cover and linework for the interior.

This can set you back between $300 minmum and it goes up from there depending on the skill and quality. There may also be different costs if you also get the copyright or if that stays with the artist and you get to use it with permission.

Think about how many books you will need to sell to "pay it off" to give you a range of what you are willing to pay.

Check out Fiverr and Artstation . There is a lot of good and hungry artists who can make your arts quick and with good quality, also there is always their portfolio where you can check if you like or not their style.
As of prices, be ready to put 400-500 dead presidents for cover and 3-4 inner arts. It's if we talk about really good arts. 150-200 for cover. If you go with black and white noir arts, which in my taste would fit your rpg its gonna be cheaper.

I think easy E covered it.

But depending where you’re contacting artists make sure they are doing commercial work. Many artists will charge extra for anything going into a commercial product. As there are specific rights that need to be covered and often that comes with the artist them selves not posting the work until later, or ever depending what’s agreed upon.

I actually paid about $1000 for each of my cover art, plus some extra depending on some other details. With other art usually being around $300.
A poster was around $2600

And honestly the extra money has all be worth it for working with professional artists that understand the process and where prepared for the work.

But probably about 2/3 is just the rights and everything to be used in commercial work.

Also, a happy artist will often be good promotion for your work. So it’s worth taking your time and finding the best artist for you if you go for it.

I'm honestly going to stick to the National Archives and NATO for now.

I'm eventually going to hire an editor/layout professional to assist me when I get everything finalized.

Whatever's left will go into the cover.

I know there's a chance this R-101's into the ground, but a good cover can make it appealing when I add the game to my portfolio of poor decisions.

There is still a lot of time as well to work on it from reading your other posts. No rush is best with something like this I think.

A lot of artists can actually do that as well, so you may find a middle ground working with one latter in the process.

RPG buyers have a higher demand for covers, and there is a skill and art to cover design.

I have seen some compelling data on cover driving sales for self-publishing of novels and the like.