When it comes to the physics of imposing these boundary conditions, there are two different ways to ask this question:
Is it possible to have a physical scenario in which the boundary satisfies both conditions? The answer is yes.
Can you physically enforce those conditions by doing something locally only at the boundary point? The answer is no.
To understand why, first note that problems with this type of boundary conditions have mathematical solutions (as pointed out by Nemo in their comment). So a physical controller that is supposed to impose the boundary condition can simply solve the equation with the given boundary condition, look at the solution to see what standard initial and boundary conditions are satisfied by the solution, and impose those standard conditions. The solution would automatically satisfy the originally intended (nonstandard) boundary conditions.
So why can't this be done locally by only acting on a point? The only nob that we have to locally control the boundary conditions is to control the heat flow. That gives you the control of one variable per point. The other variables at that point would be determined by the coupling to the neighboring points (the coupling is the spatial derivative in the equation). If you put enough heat to that point to keep it at a given temperature, the temperature of the neighboring points determines the derivative of the temperature at that point. If you put enough heat to control the derivative, you lose control of the temperature.
So let me answer the question:
- How can one simultaneously maintain insulation and constant temperature?
You can fix the temperature at that point, and make sure the derivate is also zero at that point by manipulating the initial and the other boundary condition. Setting the derivate to zero is not achieved by insulation, but rather by setting up the initial condition and control on the other boundary such that the heat flow through the boundary point happens to become zero.