Can I always expect a transform from an arbitrary CRS to WGS84 to succeed?
For 2D horizontal CRS created from the EPSG database, calls to CRS.findMathTransform(…, true) – where the true argument is for lenient datum shift – should generally succeed. For 3D CRS having any kind of height different than ellipsoid height, or for a 2D CRS of type EngineeringCRS, it may fail. Note however that even if the call to CRS.findMathTransform(…) succeed, the call to MathTransform.transform(…) may fail or produce NaN or infinity values if the coordinate to transform is far from the projection area of validity.