Summary of solution number 2 (from previous post).
After installing the lenses, mirrors and some minor alignment, took the beam profile around the expected minimum waist position (~102" from laser head). The beam profile is astigmatic as can be seen from the plot below (red / blue = x / y), so the mode matching will be suboptimal from the start.
Taking the geometric mean of the waists (w = sqrt(wx * wy)) we represent our nominal mode and find a min waist of 36.8 um (shaded region in the plot).
The OPO cavity model targets a min waist of 35.5 um (for an optimal Boyd--Klein parameter of ~2.7), but solutions exist with slightly shorter cavities and slightly larger waists which would only compromise the optimal Boyd--Klein parameter to ~2.55 for the sake of better mode matching. I think this is a good place to move out of calculation-land and see how well we can make the cavity work in reality.