Ito's integral has nothing to do with the area under a curve and no connection with rectangles, random or otherwise.
Let me try to share a motivation in the simplest language I can manage.
There's really no better justification for Ito's formula than talking about stock prices, so let's suppose we have a stock, United Marshmallow, and an old-fashioned stock ticker. Let's suppose that, at each tick, the price of United Marshmallow goes up by 1 or down by 1.
Let's say the stock price starts at 10, and the next six prices are 11, 12, 11, 12, 11, 10. In other words, the fluctuations in prices are:
$$+1, +1, -1, +1, -1, -1$$
(I know that under this model, the stock price could go negative, but let's ignore that for now.)
Let's say we're a trader and we want to come up with a strategy for trading this stock. At time $t$, all we know is what's happened at that time, so whatever amount of stock we choose to buy (or sell) at time $t$ cannot depend on information after time $t$.
Let $W_t$ be the total fluctuation in the stock up to time $t$. We get this by adding up the fluctuations up to that time. So $W_1 = 1$, $W_2 = 2$, $W_3 = 1$, $W_4 = 2$, $W_5 = 1$, $W_6 = 0$.
One simple trading strategy is to buy $W_t$ shares at time $t$ and sell them at time $t+1$. The idea here is that, if the stock has gone up a lot, then we should be more inclined to make a bet on it going up again, and if it's gone down a lot, we should be inclined to bet on it going down again. Note that $W_t$ can be negative, which would correspond to selling the stock (short sales are allowed) and then buying it back again.
The profit from this strategy is just the sum over the amount we buy at time $t$ multiplied by fluctuation in price from time $t$ to time $t+1$
$$\sum_t W_t (W_{t+1} - W_t)$$
It looks a bit like a Riemann sum, but it's not, because the price can go down, so the "base" of the "rectangle" makes no sense. And also, our $W_t$ has to be strictly on the left-hand side of the interval from $t$ to $t+1$, or else we'd be using future information.
Let's look at the cumulative profit we would get if we did this strategy at each possible time point. After time $1$, we bet $W_1 = 1$ dollars, and the next fluctuation is $+1$, so our profit so far is $1 \times 1 = 1$. Next, we bet $W_2 = 2$ dollars, but then the stock goes down, so our "profit" is $2 \times -1 = -2$. The overall profit so far is $1 -2 = -1$.
Continuing in this fashion, we get the following table:
time $t$ |
2 |
3 |
4 |
5 |
6 |
cumulative profit by time $t$ |
1 |
-1 |
0 |
-2 |
-3 |
Now let's compare this with an integral. We are doing some sort of "integral" of the function $f(W) = W$, so maybe there's a relationship with the integral of this function?
time $t$ |
2 |
3 |
4 |
5 |
6 |
cumulative profit by time $t$ |
1 |
-1 |
0 |
-2 |
-3 |
$W_t$ |
2 |
1 |
2 |
1 |
0 |
$W_t^2/2$ |
2 |
1/2 |
2 |
1/2 |
0 |
Perhaps you notice that they match up exactly if you subtract $t/2$.
time $t$ |
2 |
3 |
4 |
5 |
6 |
cumulative profit by time $t$ |
1 |
-1 |
0 |
-2 |
-3 |
$W_t$ |
2 |
1 |
2 |
1 |
0 |
$W_t^2/2$ |
2 |
1/2 |
2 |
1/2 |
0 |
$W_t^2/2 - t/2$ |
1 |
-1 |
0 |
-2 |
-3 |
We get $\sum^t W_t(W_{t+1} - W_t) = W_t^2/2 - t/2$. You can do the same calculation with any other sequence of $+1$ and $-1$ as the price fluctuations and it will still be true!
This is the mathematical fact that underpins Ito calculus.
If you take some sort of limit, time becomes continuous, $W_t$ becomes Brownian motion, and you get the famous formula
$$\int_0^t W(t) dW = W(t)^2/2 - t/2$$
Here, both sides are random variables. But the reason why the formula is true is not because of some application of the central limit theorem. It's because the mathematical fact that we checked in the example above holds for any set of fluctuations we could have chosen.
This formula extends to functions of $W(t)$, and you get the chain rule of Ito calculus.
To summarise, Ito's integral is really a way to calculate the (random) profit from a strategy which someone would make if they were trading a stock which moved up and down randomly. It's not an attempt to compute the area under any kind of curve, and it doesn't have much to do with the Riemann integral, except for a superficial similarity in the definition, and absolutely nothing to do with the Lebesgue integral, except that Lebesgue integration is required to make the "passage to the limit" part work formally.