When is the best time for ordination? When exactly is it worth considering to ordain as a monk?
Is it something that happens automatically during the path, that is, (a) special experience(s) or insight into the three characteristics?

Is strong uncomfort experienced when living the monastic life?

Thanks
When you become dispassionate in continuing the lay life or when you get enough confidence that you can successfully fend off the temptations of lay life, it is worth considering ordination. I would suggest staying in a monastery or a meditation center first, continuously for about 6 months while keeping to the 8 precepts to see if you can handle it well.