I have thought about some different custom setups, and was impressed that so far, they have all been thought up in the past (many years ago) and tested. This saved me a lot of money and work.
In the meantime, step one is figuring out if it already exists. Here are some ways I used to search for this:
Midwayusa.com. They have a lot of options for reloading, so one resource is to look at the reloading dies there. They list 11K offerings, including 5K "obscure" ones.
Rifle Reloading Dies | Dies - Reloading | Reloading Supplies
You can use this to search by increasing caliber size until you find something interesting / or not.
Similar things can be done by searching Graf and sons.
Wikipedia is an excellent resource for finding calibers. For example, suppose you are interested in something based off of the .375 H&H belted magnum. The article shows a variety (not all) of the daughter cases from it. From there, you can check each daughter case and see some examples of what was made from it.
Similar things can be done with other cases, like the 303, 222, 250 savage, large weatherby's, etc.
There are web sites like reloaders nest, snipershide, etc. that cover a lot of ground with wildcats and reloading.
The software program quickload has built into it a huge number of cartridge / bullet combinations. It is under $200, and might be an interesting resource if you are serious about spending the money for a rifle, reamer, cartridge, etc.
Another method is to do bing or google searches. Example, supposed you are interested in a 338 diameter bullet from a 378 Weatherby cartridge. A lot of them are as simple as 338-378 or 338/378.
The two ideas I had (which were also thought of long ago) were 6mm-224 Weatherby and 375 Taylor. It took a little time to find them, but since they exist, at least some other people thought they were interesting as well.
PTG has a LOT of common reamers - sort of mind boggling actually. Here is a link that shows a page - just click on the caliber range you are curious about.
http://www.pacifictoolandgauge.com/reamers2.htm#micrormrstop