I think about two main things before I even send an e-mail to the requester - am I burned out or not and does the world make any sense to me? If I just don't feel like I have my A game then I know the map will take forever to finish and the customer will get upset. If I see all sorts of logical or physical inconsistencies then I know that I'd mention them and I don't want to start arguments with the guy paying me...had that happen once...and I'm a stickler for making things realistic even if the requester isn't. The only other thing I think about is how much thought has already been put into the project...if the requester wants me to come up with everything (from the shapes of the landmasses and where the deserts are all the way to coming up with names for hundreds of places) then that's a red flag because I know endless edits are coming. Sure there's the guy who just wants a map to play a game in/on and those guys are usually pretty good to get along with cuz they're happy with whatever I come up with but the guys who want to write a book based on their short idea and 80% is stuff I come up with then that is a big no no. I know I'll rename each town at least 5 times and then move the lake over here and make the jungle a bit bigger and what if we put some mtns here (which means starting the map from scratch if it's satellite style), and how about we move this kingdom (and hundreds of labels) over there. Oh, and by the way, this is going to be in a book so I also need a black n white line drawing so it can be printed (thanks for telling me that beforehand). The more thought that has been done before you get to work means all you have to do is make it pretty.