Having looked at the site, if it's not successful enough to justify paying a great deal more than $1000 for branding and redesign, then it's not worth putting effort into managing a branding and redesign at the cost of making it successful enough where $20,000 isn't an issue. In other words, does it already look good enough that appearance is unlikely to be affecting growth among the demographic likely to use it?

Redesign of the website should be based on good user analytics and the people who can do that well are expensive relative to fiver and other find-the-low-bidder sites. They're expensive because they're busy with clients who can pay well.

Good luck.