Because you have not been a PR for 5 years yet, your assessment period starts the day you landed, Feb. 15th 2009 and ends on the day you sign the application which is Jan. 16th 2014.
You should write your absences like this:
2010-03-16 2010-03-26 Chicago, USA vacation 9
Of course you should fill in the dates you actually travelled, the places you actually visited and your actual reasons, could be visiting family, business etc.
The way you count the days for PR, any part of a day spent in Canada counts as a full day in Canada. The person you talked to at CIC did not know this but you can find it here: http://www.cic.gc.ca/english/resources/manuals/op/op10-eng.pdf on bottom of page 10 and top of page 11. It says:
6.4. Day
Section 27(2) of the Interpretation Act governs the calculation of time limits in federal statutes. Where a statute refers to a number of days between two events (and precedes the number of days with the words “at least”), both the day of occurrence of the first event as well as the day of occurrence of the second event are to be counted in calculating the number of days. For the purpose of calculating the number of days to comply with the residency obligation in IRPA A28(2)(a), a day includes a full day or any part of a day that a permanent resident is physically present in Canada. Any part of a day spent in Canada, or otherwise in compliance with A28(2)(a), is to be counted as one full day for the purpose of calculating the 730 days in a five-year period.
Therefore, for a trip like my example above, if you had left Canada on the 16th and returned on the 26th, the 16th and 26th would both be counted as days spent in Canada so the days outside Canada would be the 17., 18., 19., 20., 21., 22., 23., 24. and 25. = 9 days.
