The typical westerner is brainwashed into thinking that "freedom", "equality", "rights" are the epitome of life so when you ask a Westerner to suffer in the quest for enlightenment by cutting off his material desires to sensual pleasures, they will suddenly start screaming that it is their "right" and "freedom" to enjoy life and why should it be a barrier to enlightenment?
The catch is that our freedom is far more limited than we would like to imagine. We don't really have sexual freedom, freedom of sexual expression, freedom of religion. People are persecuted constantly for not conforming to the status quo. Freedom in America for example is a joke compared to some countries. We are deluded in thinking we are truly free. This doesn't even get into the fact that if you are engaged with samsara, you most certainly are *not* free.
Well first of all, let's define enlightenment? What is enlightenment? Is enlightenment simply all about living with unbounded love for everything and everyone? Or is enlightenment all about evolution of the human race from a lower life-form to a much higher life-form?
Its both. Don't be afraid to love everyone, its not so bad.
If you are a true monk, you wouldn't be afraid of living without food or shelter or medicine or whatever. You surrender to the Buddha or God or the Tao or whatever name the Divine has and trust that the Divine will take care of you regardless of whatever obstacle which comes up in your way.
Not realistic in the west. For one there is no free land. Everything is owned by someone. You cant just wander into the forest and start a commune, you will get arrested, fined, and so forth. You need money to at least start the process. Furthermore we have a culture of hatred towards people who don't work, so nobody wants to give anyone anything. People look upon the homeless with disgust and disdain, as less than human. People think the same of monks, they think they are just trying to be lazy and find a way to mooch of society. If we could just go wander into the forest and build a temple and start a monastic community, many of us would, but its not that simple anymore, at least not in America.
The common man got married because he wanna have a taste of the pleasures of married life. The masters got married because they need descendants to spread the teachings of enlightenment.
There are other, equally good reasons to get married besides these two. There are levels of this you simply aren't seeing. Lets examine the most basic level which is quality of life. A married couple has a better quality of life, they have more money, more mobility, more freedom. If they are both practitioners, this translates into more opportunities to receive teachings, go on retreats, and actually practice (if they are dedicated to doing that). This is just the tip of the iceburg of positive outcomes of being a householder.
If given a choice, I can assure you those masters would rather not get married because to have descendants is pretty much guaranteeing that you would be reborn again on this earth which most masters would not want to if given the choice.
Well since many of us are on the path of the Bodhisattva, the idea of returning to this world doesn't bother us much. In fact its precisely what we want to do. Most of the Masters I revere do actually want this, they want to keep helping sentient beings and they return again and again to do so. They would do anything to liberate people from suffering. They are not just trying to make a quick escape, retreating onto a lonely mountain somewhere and then vanishing forever. But we all have our ideas of what makes a person enlightened and compassionate and what doesn't.