How do I overcome the fear of losing it all on my first deal to the point of bankruptcy?

The key is this, in most areas this is the big stickler that most people are claiming is law, however, there are a few areas that do have some more obstacles that you may need to overcome such as the state of Maryland have a few laws on "Title Jumping"".

What types of obstacles did you face, and how did you overcome them?

It clearly depends on your planned use for the property (ie. personal use vs commercial use, etc) but from one investor to another I would urge you to only invest in a country in which you fully understand all of the potential challenges, including the various laws, and how you might be able to overcome them.

Make sure the discount is deep enough to overcome that.

Reality is kind of hard to overcome.

This is in most cases nothing more than an issue for that lender to overcome that consent was given, many accepted the argument, some didn't (BofA for one, depending on the type of note).

What I have found to be the biggest thing to overcome is that dang thing called fear.  

The financing is definitely a possibly hurdle to over come because I understand there are not many lenders willing to lend on investments that indeed depreciate rather than appreciate over the years.

Many of these aspects can be overcome, if you don't speak english, take someone with you, just smile alot while they translate.After you put together a list of your personal assets, strengths and weakness /short commings, then you can better identify how, when and where to get started.