Hesitating if it comes to Allah can't and shouldn't be compared to our hesitation as HIS creation. As our hesitation may come due to the fact that we may not know what will happen next or in the future, or because we don't know if anything we may do will have a benefit for us, or simply because of doubts that's why we are asked to do istikhara to ask Allah for guidance and recommended to ask more experienced people to get guidance or insight from them.
When Allah is hesitating to take the life or the soul of a believer than it can't be because HE doesn't know what will happen to this soul nor because HE doesn't know whether there is a benefit in taking it. But it is a hesitation out of mercy and compassion towards this believer (or his soul), and out of love for him, because he hates death, as it is emphasized in the hadith:
..., for he hates death, ...
and his Lord, may He be exalted, hates hurting him, as it is explained in the hadith itself:
and I hate to disappoint him.
When it comes to Allah we must always have in mind that:
...There is nothing like unto Him, and He is the Hearing, the Seeing. (42:11)
In fath al-Bary of Imam ibn Hajar al-'Asqalani the author quoted an explanation of al-Khattabi saying there are two possible interpretation of hesitation in this hadith, after saying that hesitation -in the meaning of creations like us- for Allah is not possible nor permissible, therefore an interpretation of the Arabic verb تَرْدِيد (and replacing التَّرْدِيد- repetition التَّرَدُّد - hesitation) by is used by him and others to explain:
- Maybe hesitation or hesitating referrers to the multiple occasions during life time were Allah could have taken a soul, like illnesses, accidents etc., but the believer asked Allah to heal him or save his soul!
- The second option is the sending of Messengers and asking the to repeatedly to take care of the souls of the believers and treating them well. As an example the story of Musa () and the angel of death was used. On the whole both explanations just show Allah's mercy and compassion towards the believers.
I'll answer your additional question by this hadith:
“Whoever loves to meet Allah, Allah loves to meet him, and whoever hates to meet Allah, Allah hates to meet him.”
It was said to him: “O Messenger of Allah, does hating to meet Allah mean hating to meet death? For all of us hate death.”
He said: “No. Rather that is only at the moment of death. But if he is given the glad tidings of the mercy and forgiveness of Allah, he loves to meet Allah and Allah loves to meet him; and if he is given the tidings of the punishment of Allah, he hates to meet Allah and Allah hates to meet him.” (sunan ibn Majah)
It is even not recommended for a Muslim to wish death as quoted in this hadith.
Some helpful links:
In Arabic explanation of hesitation in this hadith incluidng quotes from fath-al-bary etc.
In Arabic islamweb #53185, fatwa on the meaning of "I do not hesitate to do anything as I hesitate to take the soul of the believer" in this hadith.