To answer some of the questions I have been in a monastery. It was some of the best times in my life spiritually and physically. The day I was told my diabetes would prohibit my acceptance was like an end to my life. Because of my age and diabetes, most orders, in fact all orders I have contacted have rejected me. The abbot and my spiritual director at the monastery I was at (it was a Maronite monastery) was very much in favor of my acceptance and lobbied for the council to change their mind. But Fr. Abbot told me their answer was, "We will never accept anyone with diabetes."
I remember Fr. Corapi talking about how he was forced to leave the Franciscan monastery he was at for a completely different reason and he said removing the habit was like peeling off his skin. I can surely understand what he went through, because I would explain it the same way.
The first and most important step for me is to pay off the debts I have. That is the biggest step whether I found my own monastery or am able to find an order that will accept me.