The question you posed to me forced me to think about why I follow what I follow. And I organized some conditions to which a guide should have.
Firstly they should have sound knowledge. If you do not know with whom or what institution someone studied at, do not take from them unless it is a basic universal (such as advising to pray or holding one’s tongue). Imam Suhaib Webb studied at al-Azhar Sharif, one of the greatest Islamic institutions on the planet. Though its prestige has taken some hits in the past couple of decades, there is still a tremendous amount of good. I follow Sheik Muhammed al-Yaqoubi because I know he studied under Sheik Ibraheem al-Yaqoubi and Sheik Mekki al-Kattani, among many others for over 40 years. I searched for where Anwar Awlaki studied and I could not find information specific enough.
Another condition is good character. Good character is defined as being the character of our beloved messenger, may peace and prayers be upon him. As one follows Allah properly, then their character will improve and they will have more light. There are non-Muslim university professors who know more about Islam than many Muslims do but we do not follow them. We know from our sacred texts that worship purifies the soul and prevents us from sinning because of the effects on the heart. Compare Habib Ali Jifri and Bilal Phillips and youtube and decide who has the more Prophetic character. I think you know enough to discern.
Finally, they should have reverence and respect for anything related to Allah, the Lord of Might, and His Beloved Messenger. Sheik Muhammed would not permit me to put books, pens, or paper on the floor because these were things used in studying Allah’s law. One of the Salaf would not touch a bow without ritual purification because the Prophet touches a bow. Many of them would cry and shudder just at hearing mention of the Prophet. When Imam Malik, may Allah be well pleased with him, was looking for a teacher, he would ask them about the Prophet and he followed the one who reacted with the most reverence. Imam Malik himself was once relating a hadith and was stung by a scorpion 16 or 60 times (I forget) without noticing because of his reverence to the word of the Prophet. I was once in Damascus speaking with my cousin, a scholar, and I paraphrased a hadith. He corrected me saying that many of the righteous can feel light when they hear Prophetic hadith.
These conditions are the best I can come up with. If you can talk to Imam Suhaib again, ask him about this and he will probably give a better answer. Also, do not always assume those who describe their qualifications as doing so out of arrogance. The Prophet described himself as the messenger of Allah on many occasions and he did so without arrogance.
Also, it helps if one is a descendant of the Prophet. Allah in the Quran says “Allah only desires O! The members of the family of the prophet! That He may remove from you every uncleanness and purify you well after cleaning you thoroughly.” (33.33). Imam Muslim narrates that the Prophet said “O people, I am a human being. I am about to receive a messenger (the angel of death) from my Lord and I, in response to Allah’s call, (would bid good-bye to you), but I am leaving among you two weighty things: the one being the Book of Allah in which there is right guidance and light, so hold fast to the Book of Allah and adhere to it. He exhorted (us) (to hold fast) to the Book of Allah and then said: The second are the members of my household I remind you (of your duties) to the members of my family. He (Husain) said to Zaid: Who are the members of his household? Aren’t his wives the members of his family? Thereupon he said: His wives are the members of his family (but here) the members of his family are those for whom acceptance of Zakat is forbidden. And he said: Who are they? Thereupon he said: ‘Ali and the offspring of ‘Ali, ‘Aqil and the offspring of ‘Aqil and the offspring of Ja’far and the offspring of ‘Abbas.”
and Allah knows best.