At 30ft length each it’s far more important that you get the right gauge of wire.
i agree w this
terminate whichever is more convenient - at that length of run the wire will determine sq so much more than different (proper) terminations
I replaced banana with spades on my multi individual strand cable. I bought Audioquest spades but standard crimper did poor job. I borrowed Audioquest crimper (almost identical) from the local Audio store and it worked perfect. After crimping I soldered it heating wires first to prevent thermal expansion of the spade (to keep zero oxygen connection). I know, many purists are against using third material (solder), but connection, even if not 100%, is so tight that solder doesn't matter (electrically). If you "suck at terminating cables", then better send it to professionals - it is one time expense.
You are seriously going to spend the time and money to add terminals to wire off a reel. Unreal. Oh well, never again pretend marketing is ineffective. At least do yourself a favor and listen to the bare wire before adding the terminals. Otherwise you go the rest of your life imagining it was all worth doing.