1) Once you have the fact $$\int_{a-1}^{b}f(x)dx\ge \sum_{k=a}^b f(k)\ge \int_a^{b+1}f(x)dx,\ \ \forall a,b\in \mathbb N,$$ there is not much to prove, for at the expression $$ \int_{a}^{b+1}f(x)dx\leq \sum_{k=a}^{b}f(k)\leq \int_{a-1}^{b}f(x)dx\leq \sum_{k=a-1}^{b-1}f(k),\ \forall a,b\in\mathbb N,$$ the first two inequalities follow directly from the fact and the third one follows from the fact applied to $a-1$ and $b-1$ in the place of $a$ and $b$, respectively.
2) The proof for increasing functions is analog to that for decreasing functions. Using the fact for increasing functions
$$\int_{a-1}^{b}f(x)dx\le \sum_{k=a}^b f(k)\le \int_a^{b+1}f(x)dx,\ \ \forall a,b\in \mathbb N,$$
at the expression $$ \int_{a}^{b+1}f(x)dx\geq \sum_{k=a}^{b}f(k)\geq \int_{a-1}^{b}f(x)dx\geq \sum_{k=a-1}^{b-1}f(k),\ \forall a,b\in\mathbb N,$$ the first two inequalities follow directly from the fact and the third one follows from the fact applied to $a-1$ and $b-1$ in the place of $a$ and $b$, respectively.
3) I don't know and I can't think of any suggestions.
About the question of when the equality holds for (1), I have an idea. Note that
$\displaystyle\int_{a-1}^{b}f(x)dx = \int_a^{b+1}f(x)dx$ if, and only if,
$$
\int_{a-1}^{a}f(x)dx + \int_{a}^{b}f(x)dx = \int_a^{b}f(x)dx + \int_{b}^{b+1}f(x)dx\ \ \Leftrightarrow\ \ \int_{a-1}^{a}f(x)dx = \int_{b}^{b+1}f(x)dx.
$$
So our problem is equivalent to analyze which conditions imply that
$$
\int_{a-1}^{a}f(x)dx = \int_{b}^{b+1}f(x)dx.
$$
The simplest condition that guarantees the equality above is:
Condition 1. $a-1=b$;
Other two conditions for which the equality immediately holds are:
Condition 2. $a-1<b$ and $f$ is a constant at the interval $(a-1,b+1)$;
Condition 3. $a-1>b$ and $f$ is a constant at the interval $(b,a)$;
I guess these are the onliest cases for that the equality holds, the proof is not so difficult.