This sounds like the classic image classification challenge. The next question I would have is: is this on open world or closed world problem? Meaning, what is the world of images that the model will be exposed to in the wild. Will it only be exposed to sailboat/windmill/bird or will it be exposed to sailboat/windmill/bird and every other possible item in the world?

You also want to deploy this on a standard machine w/ or w/o a GPU? That can have implications on inference speed. But there are ways to optimise for that. The absence of a network connection is not a problem.

Also, do you have training data? If not we can probably leverage a pre-trained model for this use case where, in this case we would only need a handful of training examples.

To answer some of your questions:

Where should I look to find a quality freelancer? Not sure.

What formats should I specify for the deliverables? Depends on what tools the developer uses, for example, I would deliver files in TensorFlow export format.

What timeline should I expect? Using a pre-trained model, I could expect to deliver it in about 40 man hours.

What pricing should I expect? Probably about $6000, but that depends on the contractor.

What would a good developer expect me to provide in terms and training data? Using a pre-trained model you would only need a handful of training images. But, of course, the more the better.

What API parameters would they expect me to specify? I can't think of anything.

I have experience building and deploying these vision models. Feel free to reach out to me for more info. It's my username @ gmail.com