How much does it cost to create a freelance marketplace similar to Upwork?

My solution has always been. 1) Leverage your network but be specific in the ask "Do you know a programmer that's $20-$40 hour (likely from eastern Europe) that you've worked with and like?" 2) There so many new marketplaces jumping up focused on niches that may be worth trying (ex: http://elto.com & others). The only other solution (if you want to spend avg. ~$100/hour) is to call a local dev shop and try and get a "bro deal" / that may work great if you live in a small town and they have capacity. Hope that helps.

The best technology is whatever gets you up and running the quickest. You'll throw away the first iteration (and possibly the second and third...) anyway. What you need most in the beginning is to test your idea and get feedback, and you need it fast.

You'll find that to be the case on any outsourcing site. Focus on the reviews and comments left on a designer's profile. This will give you an idea of the quality of their work before contacting them. Further, check out LinkedIn and search for "freelance designer" or "freelance graphic design" and sift through the results. Good luck! They're out there!

I do a lot of business with people on Elance (which is now being merged into Upwork and is going away, so stick with Upwork). The real challenge for US-based workers (which you may or may not be) is the price competitive nature of jobs when competing against an international workforce. There are always going to be great workers in every country and sometimes in certain areas you just can't compete on price. For example, I do a lot of business with great people in the Philippines and their work is excellent, they speak perfect English, and they are very affordable. What I usually tell people who are first getting into the space is to be honest about that in your profile and do some jobs for near-free with private pricing so you can build up your profile with good ratings. There are some disadvantages to this approach, but I find it helps to get some jobs under your belt with employers. One of the keys is going to be differentiation. You have your industry listed but skills, language, specific experience, and other niche items are really going to help here. I'm a consumer of a lot of Upwork contractors so I'm happy to do a call and discuss my experience with you. I work with people all over the world on a regular basis and I've built my business around these assets.

Most of my friends use www.wordpress.org and http://member.wishlistproducts.com/ to create their membership sites. Hope that helps.