This is a late attempt to contribute to an interesting discussion I only recently became aware of. I hope the question is still alive.
If only one angle in the given triangle is greater than $60^o$, then the greatest inscribable equilateral triangle shares a vertex with this greatest angle and has its base on a portion of the opposite side, as in the OP's first figure.
Presuming this as agreed on, and also that the greatest equilateral triangle must share at least one vertex with the given triangle, I consider only the case where two angles are greater than $60^o$,
1) showing that the greatest equilateral triangle does not always share a vertex with the largest angle in the given triangle, while
2) revealing the conditions under which it does, and
3) the method for finding the greatest equilateral triangle when it does not.
Suppose two angles of the given triangle are greater than $60^o$ and equal.
In isosceles triangle $ABD$, the greatest equilateral triangle has $AB$ as base when the base angles of $ABD$ are greater than $60^o$ but less than $80^o$, i.e.$$\frac{\pi}{3}<\angle DAB=\angle DBA<\frac{4\pi}{9}$$ For if on $AD$ we make $AE=AB$ and construct equilateral triangle $AEF$, vertex $F$ lies outside of triangle $ABD$ unless$$\angle ABF\le\angle ABD$$If $\angle ABF=\angle ABD$, as in the figure above, then $\triangle ABD$ and $\triangle BFA$ similar isosceles triangles,
and since$$\angle BAF=180^o-2\angle ABF$$and also$$\angle ABF=\angle BAD=\angle BAF+60^o$$then$$180^o-2\angle ABF=\angle ABF-60^o$$making$$3\angle ABF=240^o$$and $$\angle ABF=80^o$$
Thus for a base angle of $80^o$, a greatest equilateral triangle can be constructed on a side of the isosceles triangle as well as on its base.
For base angles greater than $80^o$, however, i.e. when$$\angle ABF<\angle ABD$$ point $F$ lies within $\triangle ABD$, and the greatest equilateral triangle is not on the base of the isosceles triangle but on its side.

Accordingly, in the second figure (vertex $D$ of isosceles $\triangle ABD$ is out of view on the right), $F$ is within $\triangle ABD$. The maximum equilateral triangle $AHG$ is constructed by extending $AF$ to $H$ on $BD$, drawing a circle with radius $AH$, cutting $AD$ at $G$, and joining $HG$.
As $D$ becomes more and more remote, $AD$ and $BD$ approach parallelism, and $\triangle AHG$ approaches as a limit an equilateral triangle with height $AB$. If $AB=1$, the side of this limiting greatest equilateral triangle is $\frac{2}{\sqrt 3}>1$.
If two angles of the given triangle are greater than $60^o$ but not equal, then the greatest equilateral triangle is either on the side between the vertices of these two angles, or shares a vertex only with the lesser of the two angles.
In the third figure, triangle $ABD$ has angles at $A$ and $B$ both greater than $60^o$, with $$\angle DAB>\angle DBA$$
If $\angle CBD<\angle ADB$, then point $F$ of equilateral triangle $AEF$ lies outside of $\triangle ABD$, so that the greatest equilateral triangle is either $\triangle ABC$ or lies on $BD$ with a vertex at $B$.
But if, with $AD$ fixed in position, we move $D$ to the right, thereby increasing $\angle CBD$ and decreasing $\angle ADB$, until $\angle CBD=\angle ADB$, then point $F$ lies on $BD$ and $\triangle AEF$ is an equilateral triangle in $\triangle ABD$ equal to $\triangle ABC$.

Proof:
Since$$\angle EAC=60^o-\angle CAF$$and$$\angle CBD=\angle CBF=\frac{1}{2}\angle CAF$$then$$\angle EAC=60^o-2\angle CBD$$And since$$\angle ADB=180^o-2\cdot 60^o-\angle EAC-\angle CBD$$therefore$$\angle ADB=60^o-60^o+2\cdot \angle CBD-\angle CBD=\angle CBD$$
And so conversely, if $\angle CBD=\angle ADB$, then point $F$ lies on $BD$.
Now on $BD$ make $BG=AB$, and construct equilateral triangle $BGH$ equal to $\triangle ABC$.
Then vertex $H$ lies within $\triangle ABD$.
For suppose $H$ lies on $AD$:
Then since $\angle ABH=\angle CBG$, by SAS we have$$\triangle ABH\cong \triangle CBG$$But$$\angle CBG=\angle ADB$$Therefore$$\triangle ABH\sim\triangle ADB$$But $\triangle ABH$ is isosceles. Therefore, $\triangle ADB$ is isosceles and$$\angle DAB=\angle DBA$$which is false.
Therefore, $H$ lies within $\triangle ABD$, and, by the method already indicated in the second figure, an equilateral triangle greater than $\triangle BGH$ can be constructed on $BD$, sharing a vertex with the angle at $B$, which is less than the angle at $A$.
Although this case by itself, i.e. where $F$ lies on $BD$, proves that the conjecture is not always true, it appears that when two angles are greater than $60^o$ the conjecture is in fact universally false: when $D$ is remote enough so that $H$ and $F$ both lie within $\triangle ADB$, the greatest equilateral triangle inscribable on $BD$ with vertex at lesser angle $B$ is always greater than that inscribable on $AD$ with vertex at greater angle $A$.
In the daunting fourth figure, again$$\angle DAB>\angle DBA$$but $D$ is far enough out to the right in triangle $ADB$ so that $F$ and $H$ both lie within $\triangle ADB$. Extend $AF$ and $BH$ to cut $BD$ and $AD$ at $I$ and $J$, complete the larger equilateral triangles $ALI$ and $BJK$, and join $IJ$ and $KL$.

Granting the apparent concyclicity of $J,A,B,I$ and $J,L,K,I$ (I need a proof), then since$$\angle JLK=\pi-\angle JIK$$then$$\angle JLK=\angle JIB$$But$$\angle JIB=\pi-\angle JAB$$Therefore$$\angle JLK=\pi-\angle JAB$$so that$$LK\parallel AB$$Hence $LK$ cuts the sides of $\triangle ADB$ proportionally, making$$\frac{AD}{DB}=\frac{AL}{BK}$$And since$$AD<BD$$therefore$$AL<BK$$and equilateral triangle $ALI$ sharing vertex $A$ of the greater angle $DAB$ is less than equilateral triangle $BJK$ sharing vertex $B$ of the lesser angle $DBA$.
To conclude: apparently when the given triangle has two angles greater than $60^o$, if the greatest equilateral triangle shares a vertex with the greater of the two angles, it also shares a vertex with the lesser, but not vice-versa, i.e. the greatest equilateral triangle has as base either the side between the two angles greater than $60^o$, or a portion of the side opposite the greatest angle and shares a vertex with the lesser of the two angles greater than $60^o$.