Conquering vs. Settling

We read in the haftorah on Shabbos in Zecharyeh Ch. 4 verses the following (translation from https://www.chabad.org) :

(verses 1-7)

And the angel who spoke with me returned, and he awakened me as a man who wakes up from his sleep.

And he said to me, "What do you see?" And I said, "I saw, and behold [there was] a candelabrum all of gold, with its oil-bowl on top of it, and its seven lamps thereon; seven tubes each to the lamps that were on top of it.

And [there were] two olive trees near it; one on the right of the bowl, and one on its left.

So I answered and spoke to the angel who talked with me, saying, "What are these, my lord?"

And the angel who spoke with me answered, and he said to me, "Do you not know what these are?" And I said, "No, my lord."

And he answered and spoke to me, saying, "This is the word of the Lord to Zerubbabel, saying: 'Not by military force and not by physical strength, but by My spirit,' says the Lord of Hosts.

(skip to verse 11 – 14.)

And I raised my voice and said to him, "What are these two olive trees on the right of the candelabrum and on its left?"

And I raised my voice a second time and said to him, "What are the two olive branches beside the two golden vats that empty out the gold[en oil] from themselves?"

And he spoke to me, saying, "Do you not know what these are?" And I said, "No, my lord."

And he said, "These are the two anointed ones who stand before the Lord of all the earth."

As is quite evident this seems to be a broken conversation, what is Zecharyeh asking what are they and what is the response?  Rav Solevetchik explains the two olives represent the kehunah gedolah and the king from malchus Dovid that were both anointed with oil (from Rashi end of Ch. there.)  The oil was oozing out by itself (verse 11) to indicate the service in the second Temple would be so great its as if it happened by itself.  That is what Zecharyeh didn’t understand for the service in the second Temple palled in comparison to that of the first Temple.  The malach responded that it’s a prophesy about the third Temple which is merely an extension of the second Temple.  Why and how?  That is what the malach responded in verse 7 that the kedusha of the second Beis Hamikdash came about via the רוח of Hashem.  What does this mean? 

The Rambam in the end of Ch. 6 of Beis Habechirah:

ולמה אני אומר במקדש וירושלים קדושה ראשונה קדשה לעתיד לבוא ובקדושת שאר א"י לענין שביעית ומעשרות וכיוצא בהן לא קדשה לעתיד לבוא לפי שקדושת המקדש וירושלים מפני השכינה ושכינה אינה בטלה והרי הוא אומר והשמותי את מקדשיכם ואמרו חכמים אע"פ ששמומין בקדושתן הן עומדים אבל חיוב הארץ בשביעית ובמעשרות אינו אלא מפני שהוא כבוש רבים וכיון שנלקחה הארץ מידיהם בטל הכבוש ונפטרה מן התורה ממעשרות ומשביעית שהרי אינה מן ארץ ישראל וכיון שעלה עזרא וקדשה לא קדשה בכיבוש אלא בחזקה שהחזיקו בה ולפיכך כל מקום שהחזיקו בה עולי בבל ונתקדש בקדושת עזרא השנייה הוא מקודש היום ואף על פי שנלקח הארץ ממנו וחייב בשביעית ובמעשרות על הדרך שביארנו בהלכות תרומה

The Kesef Mishne says he doesn’t understand how is חזקה any better than כיבוש, why should it not be nullified as well?  Reb Chaim said (see בריסקר רב על תנ"ך סטנסל) that this was the response of the malach.  The first kedusha was accomplished via an act of conquering the entire land and that can be nullified.  In the second kedusha there was no conquest, Klal Yisroel went back with the permission of the gentiles and not all of the land was settled.  The kedusha of the land was an extension of the kedushas hamikdash, of the presence of the Shechinah and that can never be nullified (from Pnenie Harav pg. 76.)

Rav Shechter shtelz tzu another idea of Rav Solevitchik that is along the same lines.  The Mishna in the beginning of Kelim (1:6)  lists 10 kedushot and one of them is Eretz Yisroel for one may bring the omer and shtei halechem only from grain that grew there.  Why does the Mishna not mention that only in Eretz Yisroel there is an obligation of terumot, challah etc.?  Rav Solevetchik explained that the Mishna only is listing the kedusha that is an extension of the mikdash, not the laws that are relevant because of the kedusha of the land itself.  One can bring omer and shtei halechem from Eretz Yisroel because its an extension of the Mikdash.  The other dinim are because of the kedusha of the land itself, not as an extension of the Mikdash.  See more about this by my father shlita here, here (and the links there) if bikkurim is in the Mishna  here.  The entire kedusha of the second Temple comes about because of an extension of the kedushat hamikdash, not because of kedusha in the land.   

At the end of Soleveitchik On Repentance he extends this idea to teshuvah.  The verse in Nitzavim (30:3) says: וְשָׁ֨ב י״י֧ אֱלֹהֶ֛יךָ אֶת־שְׁבוּתְךָ֖ וְרִחֲמֶ֑ךָ וְשָׁ֗ב וְקִבֶּצְךָ֙ מִכׇּל־הָ֣עַמִּ֔ים אֲשֶׁ֧ר הֱפִֽיצְךָ֛ י״י֥ אֱלֹהֶ֖יךָ שָֽׁמָּה.  The verse is repetitive, it says ושב twice?  Of couse the verse is referring to the ingathering of the exile of the nation but it also referring to the ingathering of the personal soul from its exile.  He explains the first one is וְשָׁ֨ב י״י֧ אֱלֹהֶ֛יךָ אֶת־שְׁבוּתְךָ֖, it’s a quick arousing from Hashem.  The person just has to take that awakening and move forward with it, wherever the person goes, the Shechinah comes along with him.  It is a relatively easy process of teshuvah sparked by a jumpstart from Hashem.  It is a conquest of the soul that comes about via the presence of the Shechinah.  This is patterened after the kedusha of Ezra in the second Temple.  The second half of the verse וְשָׁ֗ב וְקִבֶּצְךָ֙ וכו is referring to the slow arduous process of conquering one’s own soul.  There requires a slow process of gathering ones scattered fragments of the soul that have become absorbed and lost in exile.  This is akin to the conquest of Yehoshua which took time and military prowess to be able to conquer the land.