He just wants something cool looking and memorable for the FreeBSD sponsors page and for his website. This is part of the problem with paying for designers (something I've done a bunch of times, to varying effect) --- they want to have a conversation about your brand and the message of the logo. No doubt there are productive conversations like that to be had with good designers --- but not in $500 logo projects.

To pay someone $500 and then not want to spend an hour with them making them understand your product/idea/whatever seems like a bit of a waste of money to me, likely making the results hit and miss.

Or have I misunderstood and you're saying that for $500 finding a designer than can hold that conversation is unlikely?

I think he will have a hard time getting a qualified designer to take a $500 project seriously. I have no doubt he can get something for $500, but it won't be something he likes.

You are right if you focus solely on designers from countries with a high cost of living. I'm pretty sure the friend who did my little shop's logo(you can see it at http://rightfold.io) could make something that Colin likes for less than 500$.