Note: I initially solved the problem using tedious case work (Method 2). I then figured out a more efficient method (Method 1) in which I considered whether or not the digit $3$ is used twice. I decided to leave Method 2 as a check on Method 1.
Method 1: We consider whether or not the digit $3$ is used twice.
The requirement that the number must be odd means the units digit is either $3$, $5$, or $7$.
Case 1: The digit $3$ is used at most once. Hence, we are selecting from the set $\{2, 3, 5, 6, 7\}$ without repetition.
One-digit numbers: There are three possible single-digit odd numbers, namely $3$, $5$, and $7$.
Two-digit numbers: There are three choices for the units digit. For each such choice, there are $4$ choices for the tens digit (any number other than the units digit). Therefore, there are $4 \cdot 3 = 12$ such numbers.
Three-digit numbers: The requirement that the number be less than $600$ means the hundreds digit must be less than $6$.
If the units digit is $7$, there are three choices for the hundreds digit ($2$, $3$, or $5$) and three choices for the tens digit (since we must exclude the units digit and the hundreds digit). Thus, there are $3 \cdot 3 = 9$ such choices.
If the units digit is $3$ or $5$, there are two choices for the hundreds digit (since we must exclude the units digit from the choices $2$, $3$, or $5$) and three choices for the tens digit (since we must exclude the units digit and the hundreds digit). Thus, there are $2 \cdot 3 \cdot 2 = 12$ such choices.
In all, there are $3 + 12 + 9 + 12 = 36$ odd numbers less than $600$ that can be formed if the digit $3$ is used at most once.
Case 2: The digit $3$ is used twice.
There must be at least two digits.
Two-digit numbers: There is just one, namely $33$.
Three-digit numbers: There are two three-digit odd numbers in which both the hundreds digit and tens digit are $3$'s, namely $335$ and $337$.
If both the the hundreds digit and units digit are $3$'s, there are four choices for the tens digit, namely $2$, $3$, $6$, or $7$.
If both the tens digit and units are $3$'s, the requirement that the number be less than $600$ means that the units digit is either $2$ or $5$.
Hence, there are $1 + 2 + 4 + 2 = 9$ odd numbers less than $600$ that can be formed if the digit $3$ is used twice.
Total: Combining the two mutually exclusive cases yields $36 + 9 = 45$ odd numbers less than $600$ that can be formed using the digits $2, 3, 3, 5, 6, 7$ without repetition.
Method 2: Tedious case work.
The requirement that the number must be odd means the units digit is either $3$, $5$, or $7$.
Case 1: Single-digit odd numbers.
There are three such numbers, namely $3$, $5$, and $7$.
Case 2: Two-digit odd numbers.
The units digit is $3$. Then we have five choices for the tens digit, namely $2$, $3$, $5$, $6$, or $7$.
The units digit is $5$. Then we have four choices for the tens digit, namely $2$, $3$, $6$, or $7$.
The units digit is $7$. Then we have four choices for the tens digit, namely $2$, $3$, $5$, or $6$.
Hence, it is possible to form $5 + 4 + 4 = 13$ odd two-digit numbers if we use the digits $2, 3, 3, 5, 6, 7$ at most once in each number.
Case 3: Three digit odd numbers less than $600$.
The units digit is $3$. Since the number must be less than $600$, the hundreds digit is either $2$, $3$, or $5$.
- The hundreds digit is $2$. We have four choices for the tens digit, namely $3$, $5$, $6$, or $7$.
- The hundreds digit is $3$. We have four choices for the tens digit, namely $2$, $5$, $6$, or $7$.
- The hundreds digit is $5$. We have four choices for the tens digit, namely $2$, $3$, $6$, or $7$.
The units digit is $5$. Since the number must be less than $600$, the hundreds digit is either $2$ or $3$.
- The hundreds digit is $2$. We have three choices for the tens digit, namely $3$, $6$, or $7$.
- The hundreds digit is $3$. We have four choices for the tens digit, namely $2$, $3$, $6$, or $7$.
The units digit is $7$. Since the number must be less than $600$, the hundreds digit is either $2$, $3$, or $5$.
- The hundreds digit is $2$. We have three choices for the tens digit, namely $3$, $5$, or $6$.
- The hundreds digit is $3$. We have four choices for the tens digit, namely $2$, $3$, $5$, or $6$.
- The hundreds digit is $5$. We have three choices for the tens digit, namely $2$, $3$, or $6$.
In all, the number of three-digit odd numbers less than $600$ that can be formed using the digits $2, 3, 3, 5, 6, 7$ is
$$3 \cdot 4 + 3 + 4 + 2 \cdot 3 + 4 = 12 + 3 + 4 + 6 + 4 = 29$$
Total: Thus, we have a total of $3 + 13 + 29 = 45$ odd numbers less than $600$ that can be formed using the digits $2, 3, 3, 5, 6, 7$ without repetition.
Best Answer
My thinking: When you have 11 items in which 9 are unique and 2 are the same numeral repeated, then that can be arranged in $\frac{11!}{2!}$ ways. Then, there are 10 different choices for which numeral is repeated. So we have $\frac{10\times11!}{2!}$. Finally, one tenth of these arrangements should have 0 as its first digit and those don't count. So we need to multiply by $\frac{9}{10}$
$$\frac{9}{10}\times\frac{10\times11!}{2!}=99\times\frac{10!}{2!}$$