After running into this issue once more with a fresh WordPress install, I’ve found the only way to use custom permalinks is to have them custom set up like this:
Go under Settings > Permalinks
Click on “Custom Structure” and insert like this:
/index.php/%year%/%monthnum%/%day%/%postname%/
After hours of google searching with people saying anything from disabling plugins (there were none) to reverting settings (it was a NEW site with no posts prior to changes), this is the ONLY way I’ve gotten the custom WordPress Permalinks to work in the manner I wanted. Hopefully this saves others time/frustration.