Jim's problem should not be included as part of the main conflict in "The Gift of the Magi." Della is the protagonist and the viewpoint character. It is her story from beginning to end. Her conflict arises out of her motivation. She wants to buy her husband a nice Christmas present because she loves him so much. 

Tomorrow would be Christmas Day, and she had only $1.87 with which to buy Jim a present. She had been saving every penny she could for months, with this result. Twenty dollars a week doesn't go far. Expenses had been greater than she had calculated. They always are. Only $1.87 to buy a present for Jim. Her Jim. 

Jim's conflict is never mentioned in the story. Jim is not even present until towards the end when he gets home from work. Everything that happens in the story up to the climax happens to Della. She doesn't have enough money--and yet she still keeps wanting to buy Jim a nice present. She even knows what she would like to get: a watch fob to attach to Jim's beautiful pocket watch.

In attempting to solve her conflict, Della hits on the idea of selling her beautiful hair. Impulsively she goes to Madame Sofronie and sells it for twenty dollars, just enough to buy the platinum watch fob. (Note that nothing is said about any conflict Jim might be experiencing. He may not have had any conflict at all but just decided to sell his watch to raise some Christmas money.)

One problem leads to another. Now that Della has sold her hair she sees that she looks very strange. She is afraid that Jim will be repelled by her appearance and will cease to love her. This is the way with primary conflicts in stories: one conflict leads to another one which is even more serious. Della's desire to buy Jim a nice gift was a small problem, but her fear of losing him forever is a much greater problem, and she has no means of solving this one because she has parted with the only thing of value that she owned.

She had a habit for saying little silent prayers about the simplest everyday things, and now she whispered: “Please God, make him think I am still pretty.”

She did have one recourse. She could pray to God for help. And the conflict is resolved, apparently, as a result of her prayer. It turns out that Jim not only still loves her in spite of her changed appearance, but he loves her so much that he has parted with his most treasured material possession in order to buy her a Christmas present. Prayer can work miracles. The message is especially appropriate in a Christmas story.

The main conflict of the short story "The Gift of the Magi" is only superficial. Let me try to tease out the deeper meaning. 

On the surface, there is a conflict. The conflict is that both Jim and Della, the protagonists, are poor. Moreover, it is Christmas and they want to get something for each other to show their deep love. The story starts with these words:

One dollar and eighty-seven cents. That was all. And sixty cents of it was in pennies.

However, as the story progresses we learn they each possess something of great value. Della has beautiful hair and Jim has a gold pocket watch. So, both Jim and Della have a plan. Della will cut her hair and sell it to buy Jim a chain for his pocket watch. And Jim will sell his watch to buy combs for Della's beautiful hair. 

At the end of the story, there is a surprise. Both Jim and Della have gifts that they cannot use. Combs for little hair and a chain without a watch do not work. But in the end, they are seen as wise, because they gave what they loved to another person. They outdid one another in love and generosity. What really showed was their hearts. 

From this perspective, is there really a dilemma? Probably not. It is only apparent. In the end, I am sure that they were glad to give, for in giving they received much more than they could ever imagine. 

The main conflict in The Gift of the Magi is poverty.  Because of their poverty, Jim and Delia have to make great personal sacrifices to buy the other a Christmas present.

"In "The Gift of the Magi," O. Henry uses a folksy narrator to tell the story of Jim and Delia Young, a poor young couple who buy each other special Christmas gifts, which ironically cancel each other out because Delia sells her hair to buy Jim a chain for his watch, which he in turn has sold to buy her a fine set of combs for her hair. Despite the fact that these gifts are now useless, Jim and Delia have given each other the greatest gift of all, which the narrator compares to the gifts given to the Christ child by the wise men, or magi: selfless love."

There are basically two types of conflicts in the story:

Internal conflict exists, as Della and Jim struggle with the decision to sacrifice the things that mean the most to them personally in order to provide  the one they love with a proper gift that appropriately symbolizes their love.

External conflict exists in the form of Man versus Society as Jim and Della struggle against a financially centered society in which they lack the ability or means to provide their loved one witha proper gift that appropriately symbolizes their love.

Another conflict in the story, and probably the most obvious is that the couple would like to be able to give the other something spectacular for Christmas that neither can afford because they are poor. The conflict is how each can express their love for the other through the material thing they present on Christmas Day and they find that resolved in the act of sacrifice that each was willing to commit through the useless gifts they presented made useless by each sacrifice made by Jim and Della. 

One major conflict is the couple's struggle to survive in the midst of poverty. O'Henry describes their apartment in great detail in order to show just how poor the couple is in material wealth.

Both Jim and Delia have an internal struggle as well. Delia's long, beautiful hair is her most prized possession, and she must convince herself that she's doing the right thing in having it cut. For Jim, his watch is a family heirloom that has been handed down to him. It isn't something he can go out and buy later if he should get the money. It's a difficult conflict for him as well to sell the watch.

In O. Henry's classic short story "The Gift of the Magi," Della is the protagonist, and her primary conflict is that she does not have enough money to purchase Jim a worthy Christmas present. Jim and Della Dillingham Young are depicted as a poor, loving couple, who sincerely desire to get each other a valuable Christmas present.

O. Henry primarily focuses on Della's conflict in the story as she makes the difficult decision to sacrifice her prized hair in order to purchase Jim an expensive platinum fob for his gold watch. After saving one dollar and eighty-seven cents, Della visits Madame Sofronie's salon to sell her hair. Della recognizes that her hair is the only valuable thing that she owns and willingly sells it for twenty dollars.

Once Della sells her beautiful hair, she searches every store for the perfect gift and ends up purchasing a platinum fob chain for her husband. Although Della's main conflict seems to be resolved, her solution leads to another conflict, which concerns her fear that Jim will leave her because she looks like an unattractive schoolboy.

Della reveals her anxiety that Jim will leave her by saying a quick prayer and attempting to style what remains of her hair. Fortunately, Jim's love for Della is not based on superficial material items or her outward appearance. Jim remains a faithful, loving husband and appreciates Della's sacrifice because it proves her love. Ironically, both Jim and Della's gifts are useless, but their love for each other is sincere and remains intact.