A few questions in regards to the Bnei Machir ben Menashe;
וַיֵּ֨לְכ֜וּ בְּנֵ֨י מָכִ֧יר בֶּן־מְנַשֶּׁ֛ה גִּלְעָ֖דָה וַֽיִּלְכְּדֻ֑הָ וַיּ֖וֹרֶשׁ אֶת־הָאֱמֹרִ֥י אֲשֶׁר־בָּֽהּ׃ The descendants of Machir son of Manasseh went to Gilead and captured it, dispossessing the Amorites who were there; 40 וַיִּתֵּ֤ן מֹשֶׁה֙ אֶת־הַגִּלְעָ֔ד לְמָכִ֖יר בֶּן־מְנַשֶּׁ֑ה וַיֵּ֖שֶׁב בָּֽהּ׃ so Moses gave Gilead to Machir son of Manasseh, and he settled there.
וַיֹּ֨אמֶר מֹשֶׁ֜ה אֲלֵהֶ֗ם אִם־יַעַבְר֣וּ בְנֵי־גָ֣ד וּבְנֵי־רְאוּבֵ֣ן ׀ אִ֠תְּכֶ֠ם אֶֽת־הַיַּרְדֵּ֞ן כׇּל־חָל֤וּץ לַמִּלְחָמָה֙ לִפְנֵ֣י יְהֹוָ֔ה וְנִכְבְּשָׁ֥ה הָאָ֖רֶץ לִפְנֵיכֶ֑ם וּנְתַתֶּ֥ם לָהֶ֛ם אֶת־אֶ֥רֶץ הַגִּלְעָ֖ד לַאֲחֻזָּֽה׃ Moses said to them, “If every shock-fighter among the Gadites and the Reubenites crosses the Jordan with you to do battle, at the instance of the LORD, and the land is subdued before you, you shall give them the land of Gilead as a holding.
Question number 1 - It would seem from verse 29 that Gilad was already conquered and Moshe was including it in the land Of Gad and Reuven. However from verse 39 and 40 it seems that Bnei Menashe conquered it and Moshe gave it them.
בְּנֵ֣י מְנַשֶּׁ֗ה לְמָכִיר֙ מִשְׁפַּ֣חַת הַמָּכִירִ֔י וּמָכִ֖יר הוֹלִ֣יד אֶת־גִּלְעָ֑ד לְגִלְעָ֕ד מִשְׁפַּ֖חַת הַגִּלְעָדִֽי׃ Descendants of Manasseh: Of Machir, the clan of the Machirites.—Machir begot Gilead.—Of Gilead, the clan of the Gileadites.
Question number 2 - Is there any source that connects the fact that the children of Machir were from Gilad and they conquered a place named Gilad?
וַיַּ֤רְא יוֹסֵף֙ לְאֶפְרַ֔יִם בְּנֵ֖י שִׁלֵּשִׁ֑ים גַּ֗ם בְּנֵ֤י מָכִיר֙ בֶּן־מְנַשֶּׁ֔ה יֻלְּד֖וּ עַל־בִּרְכֵּ֥י יוֹסֵֽף׃ Joseph lived to see children of the third generation of Ephraim; the children of Machir son of Manasseh were likewise born upon Joseph’s knees.
Question number 3 - Is there any source that connect the fact that Bnei Machir ben Menashe grew up with Yosef hatzaddik to the fact that they were able to conquer Gilad? Moreover, by Bnos Tzalfchod Rashi states that the verse mentions that they were from Yosef to tell us that just like Yosef loved Eretz Yisroel so did his offspring. However, here we see Bnei Menashe conquering and settling in Gilad instead of Eretz Yisroel.
אוֹמֵר אֲנִי שֶׁהָיוּ לְבֶלַע בְּנֵי בָנִים הַרְבֵּה, וּמִשְּׁנַיִם הַלָּלוּ, אַרְדְּ וְנַעֲמָן, יָצְאָה מִכָּל אֶחָד מִשְׁפָּחָה רַבָּה, וְנִקְרְאוּ תוֹלְדוֹת שְׁאָר הַבָּנִים עַל שֵׁם בֶּלַע, וְתוֹלְדוֹת הַשְּׁנַיִם הַלָּלוּ נִקְרְאוּ עַל שְׁמָם, וְכֵן אֲנִי אוֹמֵר בִּבְנֵי מָכִיר שֶׁנֶּחְלְקוּ לִשְׁתֵּי מִשְׁפָּחוֹת, אַחַת נִקְרֵאת עַל שְׁמוֹ, וְאַחַת נִקְרֵאת עַל שֵׁם גִּלְעָד בְּנוֹ; I say that Bela had many grandchildren and that from these two, Ard and Naaman, there issued from each a large family, and the offspring of the other sons were called after Bela’s name, but the offspring of these two were called after their name. So, too, I say about the sons of Machir who formed two different families, one called after his name, and one called after the name of Gilead, his son, because it was a very large family.
Ramban Numbers 32:33 ואולי בעבור היות שתי המשפחות האלה המכירי והגלעדי המועטות בשבט רצו להפרד משבטם כדי שתהיה להם נחלה רבה מהם כי ילכדוה בחרבם Perhaps it was because these two families — the Machirites and the Gileadites — were the smallest of their tribe [and would therefore have received only a small portion of the land allotted to their tribe] that they wanted to separate themselves from their tribe, in order that they should have a greater inheritance [proportionally] than the rest of them, for they could conquer it by their sword
Question Number 4 - Rashi clearly states that the Gilad clan was the largest one, while the Ramban clearly states that the Gilad clan was the smallest one. While obviously Rashi and the Ramban can argue, they both seem to be presenting it as a known fact not an opinion.