Questions:

1. Jonathan purchased land many years ago for $100,000, which is rented to tenant farmers who pay Jonathan an annual rent of $5,000. Today, the land is worth $400,000. Jonathan has just learned that he is terminally ill and does not have much longer to live. Do you advise Jonathan to:

a. sell the land now to a buyer for $400,000 and provide a bequest in his will for the cash proceeds to be transferred to his good friend Jill;
b. give the land to Jill now and let her sell it; or
c. provide a bequest in his will for the land to go to Jill after his death?

2. Same as 1., except that the land, which Jonathan purchased for $100,000, is now worth only $75,000. Should Jonathan:

a. sell the land now to a buyer for $75,000 and provide a bequest in his will for the cash proceeds to be transferred to his good friend Jill;
b. give the land to Jill now and let her sell it; or
c. provide a bequest in his will for the land to go to Jill after his death?

3. Notwithstanding your advice, Jonathan gave the land described in 2. to Jill before he died. Rather than sell immediately, Jill held the land for several years. What is her § 1001 realized gain or loss in each case if she eventually sells for:

a. $60,000;
b. $110,000; or
c. $80,000? See Treas. Reg. § 1.1015-1(a)(2).

4. During the years of Jill’s ownership of the land in 3. before sale, must she include the rent that she receives from the tenant farmers, or can she exclude the rent under § 102(a) on the theory that the rent is all a part of Jonathan’s gift of the land? See § 102(b)(1).