In “one thousand dollars,” what problem does gillian face?

The "One Thousand Dollars is a play by the O' Henry which described the situation of a boy called Gillian with 1000 dollars.At the beginning of the story the boy Gillian was given $1000 by the advocate of his uncle according the will after the death of Gillian's uncle.

But there was a condition.On the will Gillian's uncle wrote that Gillian had to give receipt of all his expense to the attorney. Basically he wanted Gillian to report to attorney how he spent the $1000 . Gillian assured the attorney about this and return to the club.

He asked suggestion to a fellow club member. But they could not reach to a decision for which way to spend money.So this caused a great problem to Gillian as he was confused how to spend this money.  

Explanation:

1.the hosts on two opposing mountains stood,  

2.thick as the foliage of the waving wood;  

3.between them an extensive valley lay,  

4.o'er which the gleaming armour pour'd the day,  

5.when from the camp of the philistine foes,

6. dreadful to view, a mighty warrior rose; in the dire deeds of bleeding battle skill'd,