This is exactly my thinking on the matter. I would rather pay more and have more time and care put into my logo than skimp and get something which necessarily had very little effort put into it. If you're doing a one-off experimental MVP, fine, pay $5 for a logo that someone threw together in a minute or two. But if you're getting ready to put some real time and effort into something, you've got to make it look good.

That said, I recognize I'm taking a risk on an untried designer here. I've benefited in the past from other people who've taken risks like that, so I consider this paying it forward. Like I said, I'll let you all know how it goes, and hopefully it pans out for me.