You've just got to learn how to face your fears. Get set into those drops and ride with the wind upon the open roads. Free your spirit! Discover a new Eugene through cycling! Just take it day by day and step by step....
Haha thanks

However regarding this exact road I am still not sure, I was riding a bus back from work yesterday and saw another pair of crashed cars. I am just not sure anything good will happen if those cars crash when I happen to be near them.
If I go for Trucker Deluxe and considering that I need 29", will I still be able to pack that bike? I've checked bags for such bikes and they seem to be 26"x26" so I wonder if 29" wheel can still be fitted in it (by removing tire or something like that)? Also if I assemble that bike, I'll be able to customize all the options such as flat/drop handlebars, fat tires (similar to mountain bike), etc?
And on the other hand, if I choose non-S&S bike and will have to pack it into that huge box, would it be possible to travel with it at all? I mean even if I pack it into the bus (which will still results in a $30-40 fee according to their website), what would I do with that box after arrival? Are there some smart boxes that can be nicely folded so that it is possible to travel with them after getting off the bus?
Eugene, mud is a very serious issue. It's important to know what type of mud were dealing with here and how pervasive it is within this particular area, in which you're cycling.
I mean, what's its consistency?
Will it be easily avoidable along the way?
Is the entire area riddled with mud holes or patches?
Just how extensive is the mud?
It's not that bad, I basically took photos of worst case places. Most of the time the ground is relatively hard, in some places it's really muddy but those places are short and I'll just drive around on grass. In some places it gets a little soft/swampy but nothing too extreme.
If your budget is between $1K and $2K, you're going to have many bikes to choose from the list.
Is this still currently your budget?
Yeah, it's still my budget. I mean I of course don't have a goal of spending all that money so if there is some good bike under 1k, I would buy it however if there is something really good and worthy in 1-2k range, I don't mind paying for that at all.