(O Allah, keep me alive in poverty and let me die in poverty...) What is its grading, given the disagreement among scholars regarding its ruling?

Al-Id al-Abassi: ... He says that regarding the hadith , the questioner asks about a difficulty he found, stating that Ibn Taymiyyah (may Allah have mercy on him) authenticated its chain of narration, while our teacher (may Allah preserve him) weakened the chain of the Shaykh al-Islam, and our teacher Abu Abd al-Rahman authenticated it. The answer is that the ruling on this hadith is an example of a valid point from a perspective that our teacher clarified in a previous lesson, which is the disagreement among hadith scholars in judging a particular hadith; some authenticate it while others weaken it. He mentioned at that time that this is similar to the disagreement among jurists as well. There are many reasons for this, including that some scholars received the hadith and attained a level of knowledge that others did not, or that some understood certain jurisprudential matters from a text in a way that others did not.
So, regarding this hadith, it is an example of their disagreement in judging hadiths because some scholars received the routes of the hadith through paths that did not reach others. The chain of this hadith, as known in Ibn Majah and others, is weak, but our teacher discovered a chain for it that is good in itself in the Musnad of 'Abd ibn Humayd or in selections from the Musnad of 'Abd ibn Humayd. The chain of the hadith, by itself and alone, is good, and there is no obstacle to explaining it for the sake of taking knowledge. Its chain is as the teacher mentioned in al-Silsilah al-Sahihah: Ibn Abi Shaybah narrated to us, Waki' narrated to us from Hammam from Qatadah from Abu 'Isa al-Aswari from Abu Sa'id al-Khudri, traced to the Prophet. All the men in this chain of narration are trustworthy, though there is some criticism regarding Abu 'Isa al-Aswari, but al-Tabarani and Ibn Hibban deemed him trustworthy, and three of the memorizers (huffaz) narrated from him, so his status is that of a trustworthy narrator. If the other routes are taken into account, the hadith is authentic. Those who did not look into this rare path—perhaps the Shaykh al-Islam did not look into it—
would naturally have weakened it. This person is excused, and that person is excused, and every person naturally judges based on the knowledge that reached him. However, the Muslim must gather what reached him, meaning what the hadith scholar gained in knowledge over others, and what the later scholar attained of this knowledge that the earlier scholar did not attain.
Or from the texts of the sacred law at this level. Another question, and this seems to be a minor one...

The Shaykh : ... to what the teacher Abu 'Ammar mentioned regarding the correct meaning of the word "the poor" (masakin) in this authentic hadith. I repeat and say that one of the precise reasons for the disagreement of some scholars in authenticating and weakening is a reason that is not, from the hadith perspective, a strong reason for weakening, which is declaring the hadith defective (mu'alla) on this basis. For example, this hadith may lead the mind of some memorizers to the meaning that the teacher Abu 'Ammar rightly denied. Generally, a very strong objection to this hadith with its specific meaning arises in my mind, and I say without exaggeration... this hadith contradicts the Qur'an. And its contradiction with the Qur'an is that Allah the Exalted said: If one understands that the Messenger (peace be upon him) is asking Allah to make him poor and destitute, while Allah the Mighty and Majestic bestowed upon him by saying: In fact, the Messenger (peace and blessings be upon him) was the richest of people in what Allah bestowed upon him of the message of the Islamic call. And you know from the books of biography and the authentic Sunnah that he would say to a Bedouin man who comes and asks him: and so on, so he would immediately embrace Islam and go to his tribe and remind them of this noble Prophet who does not know withholding but is the most generous of people. "I asked him and he gave me such and such..." This, yes?
Al-Id Abbas: ... .

The Shaykh : Yes, yes. So, in reality, this indicates that the Messenger (peace be upon him) was rich. But the matter is as he (peace be upon him) said in the other hadith: The Messenger (peace and blessings be upon him), in his perfection and beauty, just as he combined in his person the beauty of the body and the perfection of the intellect, so he (peace and blessings be upon him) combined in himself the richness of the heart and the richness of material wealth. But their material wealth did not dominate him, as is common among most rich people. So it did not occur to the mind of some hadith scholars that "the poor" (masakin) here means the poor. The Messenger is asking that Allah not make him rich, as he said: That is, this is an unsound meaning in reality for it to come from the Messenger (peace be upon him). Here, the hadith scholar does not find in the chain of the hadith anything to which he can attach to weaken it, which would increase this weakening. Weakening the taking of the hadith from the perspective of its text and meaning, but it is... in this second transmission, because the hadith has a meaning other than the one he imagined, and then he struck it with the previous verse. If the meaning had been very limited as he held, and it had no other meaning as you heard from Sayyid Abu 'Ammar, we would have had no choice but to submit to his taking of this hadith. But the meaning is not so, as you heard... A benefit: may you remember, if Allah wills, when some hadith discussions pass by you. Yes.