I guess the answer in no when $\deg(X) \geq 3$.
In fact, in this case Griffiths showed that the two rulings $L_1$ and $L_2$ in $E$ are numerically equivalent in $\widetilde{X}$ (although not algebraically equivalent in general), so the corresponding $K_{\widetilde{X}}$-negative rays $R_1$ and $R_2$ in the Mori cone of $\widetilde{X}$ coincide.
It follows that the contraction of $R_1$ is actually the contraction of the whole quadric, that is it is not possible to contract the two rulings separately.
The situation is very subtle: in fact, the completed local ring $\widehat{\mathcal{O}}_{X,o}$ is not factorial, but the fact that $L_1$ is numerically equivalent to $L_2$ implies that $\mathcal{O}_{X,o}$ is factorial.
See [Debarre, Higher Dimensional Algebraic Geometry, p. 160] and the references given therein.
You should apply a generic linear coordinate transform to the ideal and then compute the initial ideal. The matrices for which the result is the generic initial ideal is a (Zariski) open subset (Lemma 2.6, in the book). In particular the complement is of lower dimension.
Leaving distribution issues aside, if you 'pick a random coordinate transform', then you'll always find the generic initial ideal. In practice you'll find it with high probability.
There is also an implementation in Macaulay2
Edit: Here is one way to computer-prove the statements from the book. To do this I make a ring in which the coefficients of $f,g$ are extra variables. There are 10 degree 2 monomials in four variables, therefore we need a ring with 10+10+4 variables. Here is the Macaulay2 code:
S = QQ[a1,a2,a3,a4,a5,a6,a7,a8,a9,a10,b1,b2,b3,b4,b5,b6,b7,b8,b9,b10, x1,x2,x3,x4]
ba = {x1^2, x1*x2, x1*x3, x1*x4, x2^2, x2*x3, x2*x4, x3^2, x3*x4, x4^2}
a={a1,a2,a3,a4,a5,a6,a7,a8,a9,a10} -- coefficients of f
b={b1,b2,b3,b4,b5,b6,b7,b8,b9,b10} -- coefficients of g
f = sum (for i to 9 list a#i*ba#i)
g = sum (for i to 9 list b#i*ba#i)
I = ideal (f,g)
monomialIdeal I -- returns the initial ideal
Running it computes the revlex initial ideal because revlex is the default order. The output is $(a_1 x_1^2,b_1 x_1^2,a_2 b_1x_1 x_2,a_5 b_1 x_1 x_2^2,a_1 a_5 b_2 x_1 x_2^2,a_5^2 b_1^2 x_2^3)$ and thus making the $a_i$ and $b_i$ invertible we find the claimed result. For lex you have to change the variable and monomial order on $S$. One has to be a bit careful with the ordering of the variables, because M2 does not know that the $a_i$ and $b_i$ are invertible. Putting the $x_1$ last does the right thing for revlex(this needs a quick check). The Macaulay2 package that I linked is for a concrete ideal (not the generic complete intersection) like in the example.
Best Answer
EDITED to match clarifications in the question and in Sándor's answer.
The question is equivalent to asking whether the tangent cone at $x$ of the hyperplane section coincides with the hyperplane section of the tangent cone:
Blow up $x$, and denote $\tilde{\mathbb{P}}^n$, $\tilde X$, $\tilde H$ the resulting variety and the proper transforms of $X$ and $H$. Now $\phi$ extends to $\tilde \phi$, defined on the whole $\tilde{\mathbb{P}}^n$, and for every subvariety $Z\subset \mathbb{P}^n$, $\overline{\phi(Z\setminus \{x\})}=\tilde\phi(\tilde Z)$. Thus, $\overline{\phi(X)} \cap \overline{\phi(H)}= \tilde\phi(\tilde X) \cap \tilde\phi(\tilde H)=\tilde\phi(\tilde X\cap \tilde H)$, because $\tilde H=\tilde \phi^{-1}(\tilde \phi(\tilde H))$ as in Sándor's computation. On the other hand, $\overline{\phi(X \cap H)}=\tilde \phi(\widetilde{X\cap H})$.
So, whenever $\tilde X\cap \tilde H=\widetilde{X\cap H}$, your statement holds. Now we can work componentwise: assume $X$ is irreducible. It is clear that $\widetilde{X\cap H}=\tilde X \cap \tilde H$ unless $\tilde X \cap \tilde H$ has a component contained in the exceptional divisor $E\cong \mathbb{P}^{n-1}$. Since $\tilde X$ meets the exceptional divisor properly, the only case when $\tilde X \cap \tilde H$ can have a component contained in the exceptional divisor arises if $\tilde H$ does not meet $\tilde X \cap E$ properly. But if $H$ is general, so is $\tilde H \cap E=L$, and then it does meet $\tilde X \cap E$ properly!
In your example with non-general $H$, $\tilde X \cap E$ is a point which gives trouble because your $\tilde H$ happens to contain it.