Its best not to in my opinion, remember quality over quantity, more is not always better
I think if you have a good degree of emotional intelligence by delaying gratification you can do the roll one time and get a lot out of it. After a long break the second still works; however it is nothing like the first time , its not as clear-little bit more foggy or feels little dirtier even though its still pure mdma, at least in my experience it seemed this way. The first time is always magical and stands out in my mind so much more than the second and while the second feels good its simply setting yourself for a harsher comedown. Like others said it wont kill you, if you keep dosing moderate, however its kind of a personal choice whether you want to do this, just make sure it ends after this. Logically, its a better idea to do it just once, youll get the magical, enlightening, best feelings from it so I see it as doing your body a bit of a favor by having a much better time getting those brain chemicals involved in the roll back to baseline faster.
I can see your point if you haven't rolled in 5-10 years and this is a once in a lifetime opportunity; however, even in this situation I would still recommend just to do it once(and do it right by testing the stuff and having enough to do a come up) (usually having enough isnt a problem here because I see too much being used more than not ) I haven't rolled in eleven years and if I ever got the chance again onetime is all id do then take a break for a minimum of 6-12 months until I even consider rolling again.