Do it. I haven't gone all the way but I have gone from Vancouver to Kenora,
Ontario. I went alone, camped wild, cooked, ate at the occasional
restaurant, met amazing people, and it was awesome. One of my favourite
trips ever.
I too am a city boy (live a few minutes' walk from downton Vancouver) and
the time spent on the road in rural areas away from the city was just what I
needed. I do love the city, I wouldn't want to live anywhere else, but
getting away once in a while is important for me.
I'm now married and have two small kids, and it will be a long, long time
before I will have a whole summer by myself to do that again. Sure I'll be
able to go on trips and take my kids with me, but I'll have to ride at their
pace and do things to keep them entertained. Maybe in 20 years when the
kids are grown I can do it again solo.
What could go wrong? Have a catastrophic bike breakdown, with no
replacement parts on hand, and be stranded by the side of the road? Flag
down a passing farmer in a pickup truck (no shortage of them in rural areas)
for a ride into town, phone the closest bike shop, and have replacement
parts FedExed to you. Back on the road the next day.
Just go. Enjoy. You owe it to yourself. If you don't go you'll be sorry.
Trust me.
K.