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Tell me how would they do it?

The same ways and means used to get other information that it's holders do not want them to have. Not just one technique, many techniques. Sometimes poorly applied, they are government agencies. They'd probably hire a contractor for the actual work, but maybe not.

One potential means, they could hack into the Hawaii DoH computers. Why not, the Chinese and Russians probably already have. Even more likely the Israelis, who also would have good survival reasons to want to know, and to leak what they know.

Everything you described would leave a money trail which would be caught by a routine audit.
Plus whoever ordered it would have to explain why he or she is not addressing the official target list.
The tasking of “agents” for HUMINT means money (again an audit would catch you !)
Tasking of USG staff hackers would leave an internal IT audit & money trail & again the questions would quickly come,’Why are you doing this?’
Use of a contractor would leave a large money trail and another IT audit trail.
You would be shocked about the micromanagement that goes on in those places. Committee after committee after committee to get approvals, then committee after committee to review the actions taken and how the money was spent. The "excesses" of the 1960s & 1970s brought forth internal regulation piled upon regulation. Intrusive tasking & micromanagement by congressional staffers is very very common. This is why these agencies are so inefficient & lethargic. The major reason Oliver North had to be stopped from a congressional viewpoint was he was implementing a Casey idea of having an "independent espionage agency". An agency independent of congressional control because it made its own money by profiting off operations, it was "self-funding". Casey thought this was necessary because US espionage was so "broken". As you know he failed and the result was an even more congressionally managed organization. Yes you are right its possible someone inside knows. It is also possible I will win the lottery. ( I don't even play!)If he or she is an Obama appointee, they might know but very unlikely. However if they do, probably knew before he or she came to work. However I think that very very very few people know the actual facts about Obama. The only way we the public will find out is if one these court actions actually works and there is discovery with a subpoena. Even then I don't think we will get the full story, because I don't think a lot of his personal information is documented. I hope the court actions work, but I won't hold my breath.