The largest it can be is actually also the smallest it can be. In fact, if the numbers 1 through $n$ are written and the same process followed, the end result will be $(n+1)! - 1$ no matter what order you combine numbers.
Let's take a smaller set, just $\{a, b, c\}$, to see why. If you group $a$ and $b$ first, you'll end up with
$$
(ab+a+b)c+(ab+a+b)+c=a+b+c+ab+ac+bc+abc
$$
If you group $b$ and $c$ first, you get
$$
(bc+b+c)a+(bc+b+c)+a=a+b+c+ab+ac+bc+abc
$$
And just for completeness, grouping $a$ and $c$ first gives
$$
(ac+a+c)b+(ac+a+c)+b=a+b+c+ab+ac+bc+abc
$$
At the end of the $n$ numbers, you will always end up with the sum of the individual numbers, plus the sum of the products of the numbers taken 2 at a time, plus the sum of the products taken 3 at a time, all the way up to the product of all the numbers. If you added 1 to the final sum, you could factor the final result into $(a+1)(b+1)(c+1)...$ giving $(n+1)!$ in this case.
Similarly, a starting list of the number $k$ written $n$ times will result in $(k+1)^n-1$.