Doing an insulation resistance test on a 230 volt system at 230 volt and using that test to confirm satisfactory insulation resistance would not be recomended
By all means use a 230 volt test to check if anything is left in circuit,neons lamps transformers etc ,but as you know the test at 500 volt is used to see if the insulation properties are breaking down
Some people test between neutral-earth with the switches open when in your position,thereby making sure the switch wire to the light is included in the test I dont do this because if there was a fault on that leg then the transformer can be damaged by having the 500 volt applied to it in these circumstances
I would recomend do as suggested and link live and neutral together and test to earth This way the transformer is in effect shorted out and cant be damaged by a fault causing a closed circuit
This test is acceptable where lamps cant be removed or in your instance with transformers