trade up contracts = lose money 90% of the time.
You bought 10 skins for about $0.80 each, you spent $8 per trade up contract. You did that 5x, so you spent $40, roughly?
Note: Going off of Field Tested price here as of writing this post, prices will vary
Redline AK: $13.08
Cyrex's: $9.22
Trigon: $3.92
Redline AWP: $6.13
Grand Total: $32.29
You lost ~$8 here.