Has anyone encountered this? Whenever you enter or leave a settlement, you need to enter a symbol, every single time.
Rather than quick start, I chose create a new world with preset 4 characters, after kicking them out and creating my party, once I leave the city the game just decides to keep spamming asking for symbols. Had to delete the save.

This is normal and expected. But usually it doesn't start to happen until much later in the game. It is the original manual-based copy protection scheme that MicroProse implemented. At the time of release pirating was digging deep into the company profit margins. This was not removed in the current releases on GOG or Steam because an electronic copy of the manual is provided with the game. However, that can be a bit of a PITA to look through 108 pages to find the correct code. There are 20 of them. However, there are a couple of alternatives to make this task easier:

1) Use the Darklands symbols sheet that was distributed with at least one edition of the CD-ROM version (1995). Digital copies of this cheat sheet were introduced with the Darklands FAQ v.1.2.1 (Oct. '96) and have been widely distributed ever since: http://www.darklands.net/faq/darkland.pdf. If you would rather, instead of a PDF you can have it in an image file, albeit of somewhat lesser quality, in either a GIF or JPEG format.
- http://www.darklands.net/tools/symbols.gif
- http://www.darklands.net/faq/files/Symbols.jpg

2) Still, with digital copies of the cheat codes, or even the manual, "in hand" as it were, some people have reported problems of being booted out when they are playing in DOSBox with full-screen mode. This occurs when they Alt-Tab out of the game to look up the code and then Alt-Tab back in again. Sometimes the game takes that action as input, thus the player is not given opportunity to enter a correct answer. A simple work around would be to keep a printout of the code-sheet handy. Or...
A person could use a nifty solution devised by long-time Darklands community contributor 'Quadko'. His solution was to create a set of in-game graphics that incorporated the response to the interrogation right in the graphic itself. It involves replacing some of the game's original PIC files with their altered counterparts, but it is very simple to do. I have created a page about this recently, http://www.darklands.net/files/AlteredAlchemyImages.shtml, which describes it in more detail under the Files section of the "Darklands Domain".