Here is a website with several $150-$200 competitions. Some are ending in a few days, and some have relatively low entry, and it seems like multiple entries are also allowed.

http://snapitto.me/contest/marketplace

D-Pop! Labs, Inc., also doing business as www.snapitto.me (we, "Snapittome"or the "Company"), operates an Internet-based marketplace (collectively, the "Service") that connects people seeking photographs with photographers selling photographs. By accessing the Company’s website (the "Site"), using the Service, and/or registering with us, you agree to be bound by the terms of this agreement ("Agreement") and you consent to our Privacy Policy.

Modifications to This Agreement. We reserve the right, at our sole discretion, to change, modify or otherwise alter these terms and conditions at any time. Such modifications shall become effective immediately upon the posting thereof. You must review this agreement on a regular basis to keep yourself apprised of any changes. We may amend these Terms of Use at any time by posting the amended terms on the Site.
(OMITTED STUFF)

Review of Postings & Uploads. We assume no responsibility for monitoring the images, photos, postings, links, messages, text, files, video, sounds, or other materials ("Member Content") made available through the Service. We do not and cannot review all the Member Content posted or uploaded to the Site, nor do we pre-screen or approve such content.
You agree and understand that the Member Content is the sole responsibility of the person from whom such Member Content originated. Under no circumstances will the Company be responsible for any Member Content or for any loss or damage of any kind incurred as a result of the use of any Member Content posted or otherwise made available through the Service. We encourage you to report inaccurate, unacceptable, offensive or illegal content to us and we reserve the right to delete or move any Member Content posted to the Site for any reason without prior notice.
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You acknowledge that all the content provided on this Site, other than the content that you post, is provided either by Snapittome, its licensors, third party authors, vendors and members (collectively, Third Party Providers) and the underlying intellectual property rights are owned by Snapittome and/or its Third Party Providers. Elements of the Site are protected by copyright, trade dress and other laws and may not be copied or imitated in whole or in part. All product names, company names, marks, logos, and symbols may be the trademarks of their respective owners. We do not claim any copyright in any Member Content.
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Severability. The provisions of this Agreement are severable, and in the event any provision hereof is determined to be invalid or unenforceable, such invalidity or unenforceability shall not in any way affect the validity or enforceability of the remaining provisions.

That's a lot of fine print there....