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No. 1 is the easiest. See my more detailed comment below.

You have to multiply by the chance of it working to get the expected value. It's easy to write an app or a service and just never get the customers to even break even on your time. Contracting is much more likely to pay back since you just have to complete the project and the employers has to keep their word to pay.

Yeah, if you're going to talk about what's easiest in the "whats the least work" I'd say #9 would be the easiest. Chances of it working are probably pretty low for most people though.

Contracting at $100/hr will gross you $10k in 100 hrs (or about 2.5 weeks worth of work). You probably meant net so double it and you're somewhere in your ballpark.

Almost anyone that is a competent professional programmer should be able to find and execute on this much side work at a similar rate. If you're particularly good, have a particularly specialized skillset, a clearence, etc you can easily command a substantial multiple of this rate and accomplish your goal in even less time.

And you're chance of it working are very high.

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