Hi Cornered,
I can address questions 1. and 2.
1. I began my proposal in August 2009, and it will last five years. A few months into the proposal, I applied for a Bank of Montreal Pre-paid Travel MasterCard. I've written details earlier in this thread. I recently also applied for and received a Home Trust secured VISA card, for which I had to send in a $1000 security deposit. I was then informed by Home Trust that they would also need a letter from my trustee stating that the acquisition of this card would not negatively affect my performance in my proposal. Once I sent in this letter, I received the card quickly.
2. I have rented hotel rooms in person with the BMO Prepaid Card (Days Inn in Superior, Wisconsin). Different hotels take different security deposits, so all I can say is, if you don't have enough on deposit in your card it the transaction will be declined. I should think that likely $200 above the nightly rate should be enough. I realize some people have reported that prepaid cards are sometimes turned down outright, especially for online reservations. This could easily be true, and BMO themselves have told me it sometimes happens. However, it doesn't sound as if it happens often.
Hope this helps!
~Wendy