I just spoke with the Irish Consulate here in Chicago, and they were much more helpful than the last time I tried. I wanted to check and make sure I would not have a problem re-entering Ireland from any side-treks I take outside of Ireland during my stay.
Basically, it shouldn't be a problem, as long as I have a return ticket out of Ireland within the 90 days. Seems I could probably even get away with treating each flight out of Ireland as a separate return ticket and only report whatever duration I'll be in the country for each time, but they could flag me for that if it looks like I'm trying to beat the system to stay longer than 90 days. So I think reporting a 90 day stay up front and having my flight home in June on hand is my best bet. When I re-enter, just show that ticket to prove I'll be leaving. (Now if work things out and am able to come back with work permit in hand, then that's another story.)
She also gave me one very useful pointer: I should not mention that I'll be looking for work. Even though I'd be following the proper steps of 1) get a job offer, 2) apply for a work permit, 3) enter the country with the work permit (after returning home briefly in July), apparently you're not supposed to come to Ireland to look for work.
So that's good to know.
Lessons learned:
The good... Should be able to come and go more or less as I please.
The bad... Don't tell them I'm looking for work.
The ugly... There are no definite answers. Each time I enter the country, I'll be completely at the mercy of the immigration officer. All I can do is keep my paperwork in line and hope I don't run across someone in a particularly foul mood.
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