It really depends on your CPU and if/how much you plan to overclock. For normal use a 4 pin on midrange CPU is enough. When you get an i7/i9 in there you need 8 minimum possibly without much OC. The 8 pin after a little research appears to be able to give just over 300w, if thats not enough and your PSU doesn't have a second cable for extra CPU power connections, then you'll need to replace the CPU or reel in your overclocking expectations.
If you have a PSU with 2x 8 pin connectors for CPU then yes, having one in fully and another with half the pins overhanging the side of the other connector is fine aslong as you dont have to use force putting the cable in. If there is no room for the 8 pin to overhang, you can probably get an adaptor: