Disclaimer. I have no legal or immigration experience, except that I went through the process of getting a work visa, getting a different work visa when the circumstances changed and then a green card. And I did it at the same time as a bunch of others that I was working with, so we all got to compare notes along the way.
Unless you want to become a permanent resident, getting a Green Card is a lot of time, hassle and expense. If you want to cruise and work you will need a work visa, of which there are several types, many of which are also quite difficult to get unless you have the qualifications and a US employer to sponsor you.
The immigration laws were written pre-web and it seems to me that the situation you describe is a gray area, which wouldn’t raise any red flags on a B2 (visitor visa), unless you raised the issue of working here or wanted to stay for a long time. It could be argued that it is no different from an investor managing his portfolio, although it’s better to avoid arguing it at all. A B2 is for a specific period of time and you need to prove that you have the resources to support yourself for that time without working here – the longer you want to stay, the harder they will look.
If you want anything other than a B2, I strongly recommend a US immigration attorney – if you read the requirements, they seem straightforward but the attorney knows what is and isn’t acceptable. For example, there is nothing in immigration law, on the forms or in the instructions that says it is needed (or even recommended) but my lawyer had a U.S. University Professor review my qualifications and write an opinion as to what the US equivalent would be.
BTW, the visa waiver only applies if you arrive by common carrier.
Amuse yourself for an hour - Welcome to Travel.State.Gov
and click on Visas.
I can give you the name of a good attorney, PITA to deal with but really knows the issues.