mikeey,
i applied in 2003 (oct) and was done with the oath around dec. 04. i did not have to meet the judge or anyone, infact throughout my procedure there was no mention of any days missing at all. it was a normal process. my friend who was missing 5 or perhaps 6 months of the 1095 regulation did meet a judge. she applied 3 yrs after she migrated to canada but within that 3 yr period she was in india for 5/6 months. i also applied 3 yrs after i landed, but was missing a month. (i am not sure if there is a subtle difference between someone who applies 2 yrs and 6 months after landing and someone who applies after 3 yrs while missing the middle time). she presented all her documents indicating she was living in canada all those 3 yrs. she had gone to india to visit her sick father and got sick herself. she had supporting documents from the hospital where she had spent 4 months out of 5/6. the judge approved her case and she took the oath. but her process took about 1.5 yrs.
i don't want to propagate misleading info but i have heard of some similar cases where it went ok. but hearsay is just that, therefore i won't elaborate on any.
but, regarding you, did you look at the application form for citizenship? on mine it clearly said that if you have completed 1000 days you may go ahead and apply and it's upon the officer's discretion where you get it or not. also it clearly said if you have 800 something days, it's advisable not to apply. while i'm not a lawyer yet but IMO it's a legally conforming way of saying, 800 or less days, you aint getting it, 1000+ days you are probably safe. if you wish to wait, then do so but if you dont mind spending 200 dollars extra, just apply. that's all what it comes down to, 200 dollars for new application.