Okay, so that's the question about the Hilbert function. The remaining question is about Betti numbers.
Specifically, why $\beta_{ij}(S/I) \leq \beta_{ij}(S/in(I))$.
I'm trying to think how to present this without mentioning flat families ...
Let's start with an example. We'll look at $\langle x^2, (x+y)^2 \rangle$, with respect to a term order where $x$ is the leading term of $x+y$.
A Grobner basis is $\langle x^2, 2xy+y^2, y^3 \rangle$. (Note that $2xy+y^2 = (x+y)^2-x^2$ and $y^3 = y(2xy+y^2) - 2x y^2$, so these are in the ideal.
The initial ideal is $I_0 = \langle x^2, xy, y^3 \rangle$. A resolution of the initial ideal looks like (give me a moment...)
$S[-3] \oplus S[-4] \to S[-2] \oplus S[-2] \to S[-3] \to S \to S/I_0$.
The map S[-2] \oplus S[-2] \to S[-3] \to S hits the generators x^2, xy and y^3.
The first map is given by the matrix
Corresponding to the syzygies y*x^2-x*xy = 0 and y^2 (xy) - x*y^3 = 0.
Now, we can lift that back to a resolution of the original ideal. (hold on....)
Again, the shape of the resolution is
$S[-3] \oplus S[-4] \to S[-2] \oplus S[-2] \to S[-3] \to S \to S/I$.
and the map S[-2] \oplus S[-2] \to S[-3] \to S hits the Grobner basis x^2, 2xy+y^2, y^3.
The syzygies are (hold on...)
This answer will be clearer if I go back and write the generators of I_0 as x^2, 2xy and y^3.
Then the syzygies for I_0 are
And the syzygies when resolving I are
Uggh, this working in chat is a pain.
Let me explain how I am thinking first.
Look at the family of ideals <x^2, 2xy+t y^2, y^3 >.
For t=1, this is the original ideal I.
For any t which isn't 0, this is the ideal I after the change of variables (x,y) ---> (x,x+ty). In other words, this is very close to being the ideal < x^2, (x+ty)^2 >.
But it isn't quite the ideal < x^2, (x+ty)^2 >. For example, < x^2, (x+ty)^2 > contains (x+ty)^2 - x^2 = t (2xy+t y^2), but it doesn't contain (2xy+t y^2) itself.
The precise statement is that <x^2, 2xy+t y^2, y^3 > is the saturation of <x^2, (x+ty)^2> with respect to t.
And notice that, when we plug in t=0, we get <x^2, xy, y^3>.
This is true of any Grobner degeneration: We can always write it as a family, parametrized by t, where
for t=1, we have the original ideal
for t \neq 0, we have an ideal which is isomorphism to the original ideal under some linear change of variables
and for t=0, we have the initial ideal.
Is this a story you are happy with/wiling to believe in?