What to look for in an iOS developer (with checklist and answers)

Initially one might think that a developer is purely someone who needs to put some code together therefore not much can go wrong... wrong! There are many things that can go wrong. Many times I've been approached by people who thought they'd be smarter than the rest by hiring someone via oDesk, eLance etc asking me to fix their apps. Every single time it would have taken me more time to "fix" it rather than start from scratch.
You will need to rely on your programmer and therefore trust him. There is no way of being 100% sure something is going to be smooth until it's over but there are certain elements that can be good elements when assessing who you're talking to. Experience
The first thing you will want to find out is the developer's past experience. Ask how many projects he's worked on and try to understand how well this fits with what you need. Remember that apps aren't all the same. Depending on the technologies used, a programmer will be better than another. The lead developer at Facebook will probably be one of the worst game debs around.
This will also be important when helping you make decision of technical aspects such as ideal backend, authentication methods, implementations etc. The more the person has "played around" in the app development world, the better he will be able to assist and guide you. Communication
It is no secret that when VCs decide to invest in a startup they are betting on the team and communication is the foundation for any good relationship. Make sure you ask how they like to work and make sure you run away from someone who hints since the beginning at a "see you in 30days" approach. In extreme cases, you might even want to test communication by not giving all details in one email or requesting further info later to see how fast he answers and his tone, try to grasp how comfortable he is with back&forth emailing or Skype (essential for some parts of app development).
Although not essential, the developer could/should help you and teach you rather than just execute. For this reason, his ability to explain decisions or preference is crucial especially if working in a team. Pricing Be prepared to find a wide range of prices for the same spec-sheet you send out. Odds are you will be quoted anything from 600USD up to 20,000USD (for a "simple" app). There are many elements that influence the price but as we all know, cheap is cheap. It also true that bigger companies have extra expenses that a freelancer doesn't have therefore you're not paying "solely" for the service.
The best approach is to have a budget ready and along with a very clear list of requirements. Also, avoid hourly rates (common to offshore companies with big developer teams): it can lead to unexpected surprises.
Don't be afraid of talking to the developer. It is in the interest of both to reach an agreement and odds are there are elements that can be up for discussion such as timeframe, instalments, functionality etc.
 
I might be biased but I truly believe that picking a freelance developer, with a solid experience, is the best choice. There are no overhead costs tied to having a company, he is passionate about what he does (more willing to help and go the extra mile), higher flexibility with time and pay and better communication (you talk to the developer, not the sales agent).
  Questions to ask (with my answers):

• How long have you been developing apps? 3 years.
• How many apps have you worked on? 57 of mine own plus the ones commissioned by clients.
• Can I see the apps you've made? Just type my name in the AppStore, or check out my clients in the about page.
• Do you have a website? :)
• How soon can you start? Depends.
• How long will it take to get a quote? Within half a business day.
• What's the time difference? I'm in San Francisco (GMT-8).
• Are you working in a team? No, I'm a one-man-show!
• Can you create graphics? I'm not a designer but am used to coming up with layouts. I've you can invest in an app icon it'll be a good start.
• How do you charge? Fixed cost project agreed before starting, if there are changes you will be informed during development.
• Do you accept instalments? Yes, I usually do 30% deposit, 30% with he first build to test and 40% upon submission to iTunes Connect.
• Do you publish the apps on the App Store? Yes, I do everything.
• Can you publish my app on the App Store? Only if it's completely free.
• Are you open to revenue share? No.
• Do you offer any extra services? Yes, let's talk.

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