My observations after 9 years of ordination, 6 spent in the Tibetan tradition and 3 in Theravada and Chinese monasteries.
Western monks and nuns in the Tibetan tradition are in a catch 22. There is no funding for training, and no one wants you unless you are trained. For most this means either waiting until retirement for ordination, working at an outside job, or being a lifelong administrator/staff member at the centre. Also, there are some Western practitioners in Tibetan Buddhism who will not like Western monks and nuns no matter what they do.
Even if a Westerner is young enough and good in languages and moves into a Tibetan monastery in India or Nepal, there are loads of obstacles people might not think of. For example, right now, 5 monks who were studying at the monasteries in South India, and have made it through the first few years, are running into problems with the Indian administration. The government delayed the renewal of their permits to stay until after their visas had expired, so they were forced to leave the country. Three of those monks have applied for Indian visas from their home countries and again been refused. From what I understand, the situation in Nepal is even more difficult with visas. At the big monasteries there are no exceptions made, so monks often cannot move up with their class due to missing course time as no exceptions are made for foreigners. Some cannot return for years, and are not able to complete their studies. Others run out of money for airfare etc. while renewing the visas.
I found myself with no money, a visa about the expire for the third time, and no support so went from South India to Thailand. I had worked all the way through university in order to have a little money to live in India after ordination but could only get 6 month visas. No one offered to help, so I went to stay with a friend who was a monk in Thailand (after requesting permission from my Tibetan preceptor) and decided to study the Theravada tradition. A wonderful experience through which I learned a great deal, but one which was broadly criticized by Western Vajrayana practitioners. After not helping me, they criticized me for shopping traditions (I saw my loyalty to my ordination and knew if I spent another summer in Canada in robes editing legal documents in a lay office setting, it would be hard to maintain my vows).
Eventually after my teacher's suggestion to try and continue Tibetan studies and some help from FPMT, I was able to complete a translator training program in Dharamsala and have been translating for a fantastic geshe for the last 2.5 years. Now with a skill centres want me, though I realize when I am old and no longer able to perform this function I will likely find myself with no work and no means of support once again, and may have to spend old age in a government shelter type environment (I know 2 translators who this happened to after they could no longer work). The fear or the future is something I have decided to live with as a cultivation of renunciation. I realize that right now I have an amazing opportunity to serve the dharma and accumulate merit. But to say it is not a concern would not be honest.
To compound the difficulties, there are a number of not so well-adjusted people in our tradition who were ordained by lamas with good intentions. This means that often people in robes might not behave well, become rigid dogmatists, or be seen as mooches. It is very unfortunate. Also, when people ordain later in life it is far more difficult to challenge one's habitual tendencies or live in a community. I don't necessarily think people should be ordained if they will continue to live alone in their apartment and work. HHDL has guidelines on his webpage that make it clear he will nor ordain people under those conditions.
The way to handle this would be to train young monastics so that they can serve the centre in some capacity, though many centres don't see the long-term benefit in this. Rather than send someone to India/Nepal and fund their translator training, for example, to save money they would rather have someone in the community translate even if that means the teacher will be severely limited in what they can present, and the quality will be lower. Rather than fund a Westerner in a monastery people want to save for their own retreats and empowerments. This is fine, people are free to make choices, but if no one is interested in supporting education for Western monks and nuns it seems a bit hypocritical to then complain about them being not qualified.
To close, though, I want to tell would be monks and nuns not to lose hope. Try to build some skills to be able to serve the Buddhist community, and continue to help others according to your present capacity. Most importantly, be kind and courteous, and try to maintain good relationships with everyone. Over the last two years, I have to say there are some laypeople who have shown me tremendous kindness and appreciation, and have helped from time to time. It did take many years of hardship in the beginning, but maybe that was about my karma. If you remain determined eventually people will see that determination, and slowly you might find that support manifests. Just the other week someone I met through this very board gave me a beautiful thangka to support my practice. Last year several people in Canada who I knew as a teenaged dharma practitioner organized funding for Geshe la and I to sponsor empowerments with his uncle, the abbot of Sera Jey, for a large group of monks and nuns in India.
Conditions are hard but things can change when you feel you are at the end of your rope.
A foolish man proclaims his qualifications,
A wise man keeps them secret within.
A straw floats on the surface of water,
But a precious gem placed upon it sinks to the depths