I think the sad thing is the contrary to some people's opinions, this is not limited to small "cowboy" companies, it can happen from the smallest to the biggest

I think the sad thing is the contrary to some people's opinions, this is not limited to small "cowboy" companies, it can happen from the smallest to the biggest and it is a mixture of competence, management, desire for profits etc. as it is in most companies. The biggest difficulty is that you are paying a premium for intangibles when you talk designs and branding. If you absolutely know that your current brand is useless then anything is better than nothing but also you probably don't have to do very much to get better before the returns are diminishing. Otherwise for design work, although the result might look "OK", it is hard to see how they would justify the money, although of course they will just like Tropicana justified their failed redesign. I would normally say that you have to know enough about something to pay somebody else to do it well but here the OP does seem to know roughly what is going on so it might just come back to a more formal kick-off process and not getting caught up in the excitement that you just start and worry about it later. Clearly this company could have done a good job so it is not about ability, just management and scoping it properly.