ואם תקריב מנחת בכורים לה. The Toras Kohanim has a derash on the word אם indicating the omer may or may not be offered that עתידה שתפסוק ותחזור, for now we don't have a korban omer but it will return. But all korbanot are not offered now so why single out the omer? The Meshech Chachma explains when it comes to korbanot מקריבין אע"פ שאין בית, the kedusha of the original Mikdash lasts forever after it was erected but in regard to the kedusha of the land itself the first kedusha of the land was batel and only came back to be everlasting through the conquest of Ezra. Therefore, the omer which must be offered from grain of E.Y., in between the first golus and the conquest of Ezra would not be able to be offered because the kedusha of the land did not exist at that time and it is that timeframe which the Sifri is referring to.
The Toras Hakodesh (volume 3 siman 30) goes a step further. The Or Sameach (Temidim 8:3) explains that the omer and shtei halechem are exempt from the obligation of terumot since they are called ביכורים which are exempt from terumot. In other words, sometimes the omer korban has the status of bikkurim. Nowadays, even though the kedusha of Eretz Yisrael remains, there is no obligation on a Biblical level of terumot since the obligation of teruma is only when the majority of Jews come into Eretz Yisrael, ביאת כולכם (Rambam Terumot 1:26.) What about other obligations that stem from the kedusha of the land, would they also have this condition of ביאת כוכלם or is it limited to teruma and challah? Simply understood it should be a גזירת הכתוב for terumah and challah but one could argue that it is not a mere halacha in the obligation of terumah and challah but is a halacha in defining when the kedushas ha'eretz is complete and would apply to other agricultural obligations well. Argues the Toras Hakodesh, in that case we can say that the bikkurim would not apply unless there is ביאת כולכם and the omer offering having the status of bikkurim will not apply as well. In this vein the Sifri is not just talking between the time of the two בתי מקדש but nowadays as well even though מקריבין אע"פ שאין בית but the omer can't be offered for it needs ביאת כולכם to establish the kedusha of the land regarding agricultural obligations.
The Gemarah Rosh Hashana (13a) asks how the omer was offered immediately after entering Eretz Yisrael is if grew to be a third of its growth in the hands of gentiles? The Minchas Chinuch (302) asks why did the Gemarah asks that it grew in chutz laeretz since Eretz Yisrael was not imbued with the kedush of כיבוש yet? The Minchas Avraham on the Toras Kohanim suggests that for the omer there was no need for the formal קידוש of the land through כיבוש but it suffices that the land had the status of the promised land of Eretz Yisrael and for that there is no need for an act of כיבוש to establish the obligation. It comes out according to his argument that there is no need for כיבוש to offer the omer but rather the status of Eretz Yisrael which applies even without the formal kedusha (as explained by my father, 'kedushas eretz yisrael'. In that case, the Mesech Chachma's assertion that there is a need for kedushas ha'aretz to offer the omer would be incorrect.
The Mishna in Kelim (1:6) says ארץ ישראל מקודשת מכל הארצות. ומה היא קדושתה? שמביאים ממנה העומר והביכורים ושתי הלחם. Why does the Mishna not list terumot and maasarot? And the Gra takes out bikurim from the list, why? Rav Aharon Kotler (Osef Chidushay Torah #33) explains that the Mishna is referring to halachot that apply because of the kedusha of Eretz Yisrael itself as the promised land not halachat that are established due to the kedusha of כיבוש. If so, the obligation of the omer and shtei halechem does not depend on the kedusha of כיבוש but will be limited to the actual promised land. That is why the Ran Nedarim (22a) says that one can not bring the omer from grain of עבר הירדן because even if it has kedusha, it is not part of the actual promised land. The Gra removes bikurim from the Mishna since he holds it is a mitzvah that depends on the the kedusha of the land which depends on כיבוש, not on the actual land of Eretz Yisrael proper (it depends on who to rule like in a Mishna Bikurim 1:10.)
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