Can You Delegate Someone to Perform `Umrah on Behalf of a Dead Person?
Question

There is a person I got to know in Makkah Al-Mukarramah who I delegate from time to time to perform the obligation of `umrah on behalf of my mother and grandmother who are deceased. I also ask friends and family if they want to delegate this man to do `Umrah on behalf of their deceased loved ones. 
I pay 300 dirhams to this deputy for each deceased person on whose behalf he performs `Umrah. My role is that of a middleman between this deputy and my family and friends. I take it upon myself to pay the money transfer fee from my own money, i.e., approximately 20 dirhams for each transaction, more or less. 
My question is: 
Is what we are doing Makrooh (disliked) or Mustahab (recommended)? 
Will I have any reward for making things easy for my family and friends and for my efforts in going to the bank to do the transfer and paying the transfer fee from my own money without them knowing about this? 
I know that it would be better for me to do `Umrah myself on behalf of my mother and grandmother, but to make things easier and to increase the number of times `Umrah is done, we are doing it in this way. 
Please note that what I am doing is sincerely for the sake of Allah and without seeking any financial or material gains. May Allah reward you with all good.
Praise be to Allah.Can we perform `Umrah on behalf of someone else?
There is nothing wrong with doing `Umrah on behalf of the deceased or on behalf of one who is alive but is unable to do `Umrah himself because he is too old or is sick with a chronic disease from which there is no hope of recovery. The one who does that is doing a good deed and will be rewarded , in sha Allah. 
Can you delegate someone to perform `Umrah on behalf of a dead person?
There is nothing wrong with giving money to someone who will do that, but you should look for one who you think is good, righteous and has knowledge of the rulings, provided that the deputy will do what he has been appointed to do himself or will tell the one who appointed him that he is going to appoint another person to do it, because the one who appointed him may accept him delegating it to another person because he trusts him, but he may not agree to delegating it to someone else. 
Shaykh Ibn `Uthaymin (may Allah have mercy on him) was asked about a person who appointed someone to do Hajj on behalf of his mother , then after that he found out that this person had taken on a number of such appointments. What is the ruling in that case? Please advise us, may you be forgiven. 
He replied: 
“What a person should do is be firm in his dealings with people and should not delegate things except to a person whose religious commitment he feels at ease with in the sense that he is trustworthy and knowledgeable of what needs to be done for the task for which he has been appointed. If you want to appoint someone to do Hajj on behalf of your deceased father or mother, then you have to choose someone whose knowledge and religious commitment you trust, because many people are very ignorant about the rulings on Hajj and they do not do Hajj in the proper manner, even though they may be trustworthy in and of themselves, but they think that this is what is required of them and they make many mistakes. Such people should not be appointed to do Hajj on behalf of others, because of their lack of knowledge. And some people may have knowledge but they are not trustworthy, so you see them not caring about what they do or say during rituals of Hajj, because they are not trustworthy and are lacking in religious commitment. Such people should not be appointed either to do Hajj on behalf of others. 
The one who wants to appoint a person to do Hajj on his behalf should choose the best in knowledge and trustworthiness of those whom he can find, so that he will do what is required of him in the best manner. 
With regard to this man whom the questioner says he appointed to do Hajj on behalf of his mother and heard later on that he had taken on a similar task for others, it depends. Perhaps this man who took on the task of doing pilgrimage for others appointed other people to do them and he performed Hajj on behalf of the one who appointed him. But is it permissible for a person to do that, i.e., is it permissible for a person to take on the task of performing Hajj or `Umrah on behalf of a number of people, then not do it himself, rather he delegates it to other people? 
In response to that we say that it is not permissible and is not allowed, and it comes under the heading of consuming people's wealth unlawfully, because a lot of people do business in this manner, so you see them taking on a number of pilgrimages, whether Hajj or `Umrah, on the basis that they are the ones who will do it, but then they delegate it to other people for less than the money they received for that, so they earn money in a prohibited way and they give the job of doing these pilgrimages to people who may not be approved by the people who appointed him to do this task. People should fear Allah with regard to their brothers and their own selves, because if they take this money they have taken it unlawfully, and because if a person is entrusted with something by his brothers on the basis that he is the one who is going to perform Hajj or `Umrah, it is not permissible for him to delegate that to someone else, when the one who gave him the task of doing this Hajj or `Umrah may not approve of this other person.” (Fatawa Ash-Shaykh Ibn `Uthaymin, 21/154) 
What you are doing by acting as an intermediary between the person who is delegating the action and the one who is doing `Umrah on his behalf, and spending from your own money on the transfer fees -- all of that is righteous deeds for which there is the hope that you will be rewarded, in sha Allah, because the one who guides others to do good is like the one who does it. 
And Allah knows best.