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For me, I personally hate paying retail the way it is so I swipe my card with the stink face on pretty regularly now. If I miss out on a release then im cool with that. ive had enough gems come through my house to be over the whole wow factor for shoes these days.
As far as what you should do:
I think if you say $240 is too much to pay on the regular then don't pay it. Just be willing to accept defeat if/when you miss out.
The hassle.... Shoes cost me $180 after tax. If I get from finishline then its $188 shipped. you paid an extra $52.00. If its not inconvenient for you to do the raffles then by all means go for it. I personally don't live close enough to malls to want to drive through rush hour after work for a "chance" to get shoes. Too tired/lazy at the end of my day. I just want to eat, spend time with my family, ban on people on NT ( ), then play video games.
You can also mix it up. Only pay the convenience fee for high priority releases. The ones you are iffy on just try your luck.
Hopefully this was helpful
$240 isn't a lot, the fact that I paid $240 on a shoe I could have gotten for about $180 something shipped and everyone got fairly easily because it was a general release is what bugs me. I now know that these are harder to get so a $240 price I wouldn't mind, but the convenience price is around $400 to $500 I believe and that I'm not willing to pay lol but for the most part, I live within 10 minutes of each mall and since I'm in a wheelchair when at the mall, I don't mind doing the whole raffle thing since both malls are close. I guess the convenience factor price is worth it for a shoe I want that I know will be harder to get than the Oreo 5's. But, for shoe's that are on the level of the Oreo 5's release and hype wise I wouldn't mind trying my luck with the raffles. I'm new to all of this so it's still a learning process for me and these Oreo 5's were a measuring stick in a way. I really appreciate the help and all the clarity of mind you have given me with all the questions I have had for you, thanks bigj505