I chose to have the toolpath on the line
For the machine along a line strategy, you can select multiple crossing vectors, open vectors etc so VCarve Wizard does not try and orientate the vectors for this strategy. For Version 3 we will grey out the climb / conventional option when the "Machine Vectors ... On" option is chosen, sorry for the confusion.
With regard to which way round the vector is climb and conventional, this depends on if the vector is representing an 'outside' profile or a 'hole'. When you choose machine 'Outside' or 'Inside' you give VCW enough information to be able to calculate the required direction and VCW will orientate all the nested vectors for the correct cutting directions. If you just tell it to machine along the centre of the line, VCW does not know for a particular vector which side of the cut represents the finished part and so which direction to cut to make it climb or conventional.
I hope this makes sense, if not just ask again