Helping the needy and giving charity to the poor is one of the best acts of worship and obedience. Allaah says (interpretation of the meaning): 

“Those who spend their wealth (in Allaah’s Cause) by night and day, in secret and in public, they shall have their reward with their Lord. On them shall be no fear, nor shall they grieve”

[al-Baqarah 2:274]

The greater the need of the poor person, the more mustahabb it is to give charity, because meeting needs and helping people are among the most important reasons why charity is prescribed. 

It was narrated from ‘Umar ibn al-Khattaab (may Allaah be pleased with him) that the Prophet (peace and blessings of Allaah be upon him) said: “The best of deeds is making the believer happy, such as covering his ‘awrah, satisfying his hunger or meeting his need.” Narrated by al-Tabaraani in al-Mu’jam al-Awsat, 5/202; classed as hasan by al-Albaani in Saheeh al-Targheeb, 2090. 

Shaykh Ibn ‘Uthaymeen said: 

If it is said: Which of these eight categories is most deserving of receiving zakaah funds? We say that the most deserving is the one where the need is greatest, because all of them meet the description, so whichever need is greatest should be given priority. Usually the need is greatest among the poor, hence Allaah started with them and said: (interpretation of the meaning): 

“As-Sadaqaat (here it means Zakaah) are only for the Fuqaraa’ (poor), and Al‑Masaakeen (the poor) and those employed to collect (the funds); and to attract the hearts of those who have been inclined (towards Islam); and to free the captives; and for those in debt; and for Allaah’s Cause (i.e. for Mujaahidoon — those fighting in a holy battle), and for the wayfarer (a traveller who is cut off from everything); a duty imposed by Allaah. And Allaah is All-Knower, All-Wise”

[al-Tawbah 9:60]. End quote.  

Majmoo’ Fataawa Ibn ‘Uthaymeen, 18/question no. 251. 

It says in al-Mawsoo’ah al-Fiqhiyyah (23/303): 

Giving to those who are entitled to zakaah is not all the same, rather there are distinctions. The Maalikis stated that it is recommended for the one who is giving zakaah to give priority to those who are in hardship over others, and to give them more than to the other categories. End quote. 

If the poor person or beggar is incapable of working, and is prevented from working by sickness or calamity, then he must be given charity. Allaah says (interpretation of the meaning): 

“(Charity is) for Fuqaraa’ (the poor), who in Allaah’s Cause are restricted (from travel), and cannot move about in the land (for trade or work). The one who knows them not, thinks that they are rich because of their modesty. You may know them by their mark, they do not beg of people at all. And whatever you spend in good, surely, Allaah knows it well”

[al-Baqarah 2:273]

Sa’eed ibn Jubayr said: 

These are people who have been injured when fighting for the sake of Allaah, and have become chronically sick, so they are given a share of the wealth of the Muslims. 

Al-Durr al-Manthoor, 2/89 

What is meant is that the criterion with regard to charity is need and want. If it seems to you that one beggar is in greater need than the other, then he should be given charity first. 

If the amount that you want to give in charity is sufficient to meet the need of both beggars, then share it between them, but if there is only enough for one of them, then in that case there is no sin on you if you give it to either of them, but try to conceal that from the other, so that he will not feel any resentment or envy. 

Shaykh Ibn Baaz (may Allaah have mercy on him) was asked: if a man gives zakaah on his wealth, and it is a small amount such as two hundred riyals, is it better for him to give it to one needy family or to divide it among a number of needy families? 

He replied: 

If the amount of zakaah is small, then it is better to give it to one needy family, because sharing it out among a number of families when it is so small will reduce its benefit. End quote. 

Fataawa Ibn Baaz, 14/316 

And Allaah knows best.