If someone regularly fasts the six days of Shawwal, are they obligated to fast them every year?
A person is not obligated to fast the six days of Shawwal every year, even if they have made it a habit. However, someone who regularly performs a good deed should not abandon it as long as they are able.
Is it permissible to pay the expiation of an oath to a charitable party as it feeds the poor and needy such as Tkiyet Um Ali?
There is no harm on authorizing someone to handle the expiation of another to the poor and needy, since Shafiee's jurists stated that authorizing someone for the purpose of distributing Zakah, expiation and vow is permissible as stated in [Mughni Al-Muhtajj,vol.3/pp.237]. At last, the intention of the person who intends to authorize someone else suffices in this regard. And Allah Knows Best.
How to pay Zakah (obligatory charity) due on articles of merchandise?
Articles of merchandise are estimated by their whole sale market price at the end of each lunar year, and (2.5%) of their value is paid as Zakah whether it (value) went up, or down compared to actual purchasing price, and whether the increase (profit) was in the article itself such as an increase in the animal`s weight, or in the prices themselves. And Allah Knows Best.
What is the ruling on congratulating others on the arrival of Ramadan?
Congratulating others on the arrival of Ramadan is permissible.
If someone does it to express their love for worship and the blessings of Ramadan, and congratulates their fellow Muslim, they have done something good.
The Prophet ﷺ said: "Shall I not tell you something that, if you do it, you will love one another? Spread peace (Salam) among yourselves." [Narrated by Muslim]
Giving Salam is a prayer for peace and safety.