[ultrasaurus]

Hence the "healthy" part (I agree with the general tone of the comments that this instance seems a little less than healthy).

In general (like an average 99designs user) a long term process where you win 10% of the bids can be entirely fine. Especially if the trade off is towards spending more time designing and less time in meetings.

(Worth noting too, many designers submit slight variations of the same design to multiple contests)