I aim to pay $80-$99.
Shipped? Not bad, best I usually see is ~$100-120.
Apply for the chase southwest cc get 50k points after $1k spend redeem for $500 in gift cards.

You mean you waste the 50k on GC and not on SW flights?
Wouldn't you be getting sooo much more value out of the points if you used them for travel (instead of 1 cpp with GC's)?