I've already posted an answer on this thread, but I found another example I'd like to describe separately. Let $r > 0$ and consider the following problem, coming from compound interest or as one definition of $e^r$:
Show that $f(n) = (1 + \frac{r}{n})^n$ increases with $n$.
One generalize the problem strategy is to allow $n$ to be a continuous variable (probably this trick could have its own article). Now, see if you can prove that $f(n)$ still increases. If you take this mindset, it's natural to use the definition of $n$th power for $n \in {\mathbb R}$ and write
$f(n) = e^{n \log(1 + \frac{r}{n})}$
And the problem has reduced to showing that
$x \log(1 + \frac{r}{x}) = \int_0^1 \frac{r}{(1 + \frac{sr}{x})} ds$
increases with $x$, which it clearly does. (Here we've used the integral definition of the logarithm, but written in a way typically helpful for analyzing such products.)
Another problem that can be solved through allowing a discrete parameter to be continuous is to prove Stirling's approximation for $n!$ (although to make that proof very clean you can also use other labor saving tricks like Taylor expansion by integration by parts and the dominated convergence theorem).
If you ran into this problem from compound interest, or you were hoping for something more elementary which did not use such a heavy understanding of the exponential function, then you probably want to find a different proof. But finding a different proof still seems to require "generalizing the problem", but in a different way.
Another proof, goes as follows. Imagine that interest at a rate $r$ works as follows: once an amount of money is invested, the value of each unit after a time $t$ is given by $(1 + tr)$. That is, the value of the money grows linearly. Now imagine you had the opportunity to withdraw and immediately reinvest your money at a time of your choice. Having this ability would allow you to raise more money, because it would allow you to accrue interest on the interest you've already earned (hence the name "compound interest"). With this interpretation, the number $(1 + \frac{r}{n})^n$ is the value of each unit of money after time $1$ and $n$ regularly spaced compoundings.
The proof now goes as follows: if you had a choice of when these compoundings would occur, then the more compoundings the better, and the best way to allocate $n$ compoundings is to have them occur at $n$ regularly spaced time intervals. That is, we interpret
$(1 + \frac{r}{n})^n = \max \prod_{i=1}^n (1 + a_i r)$
under the constraint that $0 \leq a_i \leq 1$ with $\sum a_i = 1$.
For example, it is better to have one compounding than to have none at all, because after withdrawing and reinvesting the money, now not only does the initial investment grow linearly, but also the interest you earned before the withdrawal grows linearly. For the same reason, given $a_1, \ldots, a_n$, the opportunity to compound once more during, say, $0 < t < a_1$, would allow you to increase the amount of money at all later times.
The fact that the best choice of $(a_1, \ldots, a_n)$ is to have $a_1 = a_2 = \ldots = a_n = \frac{1}{n}$ is the principle that the largest product you can obtain when the sum of positive numbers is fixed is to have all the terms equal. This is easy to check with two variables: you can either find the largest rectangle to fit inside an isosceles triangle, or otherwise just note that if $a_1 \neq a_2$, then changing to $a_1' = \frac{(a_1 + a_2)}{2} = a_2'$ gives an improvement for $(1 + a_1 r)(1+ a_2 r) < (1 + a_1' r) (1 + a_2' r)$. The case of $n$ variables actually follows from this observation.
So if you really wanted some elementary solution to the problem, this one would do. It's an interesting example because you can see that either solution involves some kind of generalization, but the two generalizations are unrelated to each other. The first one does not need to / is unable to consider these non-even partitions. The second does not need to / is unable to consider fractional $n$.
By the way, does anyone know how to prove in an elementary way (i.e. expanding) that $\prod_{i=1}^n (1 + a_ir)$ tends to $e^r = \sum \frac{r^k}{k!}$ as $\max |a_i| \to 0$ with $0 \leq a_i \leq 1$ and $\sum a_i = 1$? An easy solution goes by writing the product with the exponential function so that you get the exponential of $\sum \log(1 + a_i r) = \sum \int_0^1 \frac{a_i r}{(1 + s a_i r)} ds$.
You can then integrate by parts (i.e. Taylor expand) to obtain
$\sum a_i r - \sum \int_0^1 (1-s) \frac{(a_i r)^2}{(1 + s a_i r)^2} ds$. Now, $\sum a_i r = r$ is the main term. After you take $\max |a_i|$ to be less than $.5 / |r|$, the error term is bounded in absolute value by $C \sum (a_i r)^2 \leq \max \{ |a_i| \} \cdot \sum a_i |r|^2$. I can, of course, move this question to a different thread.
EDIT: I realized later on that there is a completely elementary proof, and it is also completely obvious even though I didn't think of it. Namely, you expand $(1 + \frac{r}{n})^n$ into powers of $r$, and it is easy to see after a little algebra that each coefficient increases with $n$. I still find the other solutions interesting, but this turns out not to be a good demonstration of how generalizing can make a problem easier. By the way, the last question I had asked was answered in this thread:
A limiting product formula for the exponential function