Sorry to say, but I very much doubt you'll be approved with this long an absence, even if you do have an "understanding" IO. Plain facts of the matter are that your primary residence was overseas for 2 years - you not only lived there, but worked there for a non-US company.
Your visits back to the US count for very little at all, and certainly do not put you in the "under 6 month" category; each time you re-entered the US, you already had intent to return to your job abroad. Family medical problem, re-entry permits and the like, are not sufficient to preserve residence for naturalization purposes.
Put bluntly, you cannot simply buy US citizenship by purchasing a return airline ticket every 5 months. IOs are not so short sighted that they can't see you were trying to play around the rules... sorry.
Your visits back to the US count for very little at all, and certainly do not put you in the "under 6 month" category; each time you re-entered the US, you already had intent to return to your job abroad. Family medical problem, re-entry permits and the like, are not sufficient to preserve residence for naturalization purposes.
Put bluntly, you cannot simply buy US citizenship by purchasing a return airline ticket every 5 months. IOs are not so short sighted that they can't see you were trying to play around the rules... sorry.