Does loving your shaykh matter spiritually?

Loving one's shaykh for the sake of Allah has approval in the hadith narrated by Abu Musa may Allah be pleased with him. [Musnad Abi Ya'la, as quoted in Fath al-Bari 9/114] That love is part of adab, which means respect.

The Beloved Prophet ﷺ said, "Allah said, 'Those may be assured of My love who love each other for My sake, who sit with each other for My sake, who visit each other for My sake and who spend on one another for My sake.'" [Muwatta Imam Malik 1710] The reference is made to the virtues of the company of those who meet each other for the sake of Allah, as the disciple and the shaykh, or the fellow disciples.

Abu Dharr may Allah be pleased with him once asked Allah's Prophet ﷺ, "O Allah's Prophet ﷺ! What about someone who really loves a certain group but is unable to do what they do?" The Beloved Prophet ﷺ replied, "O Abu Dharr may Allah be pleased with him! You will always be with those you love." [Sunan Abi Dawud 5126] The hadith clearly indicates the virtue of those who love their teacher.

Quite often, a shaykh would initiate a person who is lesser in spiritual development, solely for the reason that he possesses the requisite desire. The readiness and enthusiasm with which the seeker absorbs and practises the teachings of the shaykh will determine his progress, and that is the key to success on the path of Tasawwuf.