Top 5 Dilemmas for a big trip like this

When undertaking a big trip like this, there are a number of issues that come up. It just isn't as easy as saying, "I think I'll hop on the bike and go!" I wish it were that easy, and I guess technically it could be. But if I want to make a splash out of this, and do some charitable good at the same time, it just ain't that easy.
Dilemma #1 - Who's going?
Do I bring more than one person? Do I bring anyone else? For safety's sake, it's almost stupid to try this alone. Sure, one flat tire in the middle of "nowhere, British Columbia" and I become bear food.
The potential for more questions multiplies with each person you decide to add to the trip. That's not necessarily a bad thing, but it complicates everything exponentially. For example, Matt & I can go (that's two bikes) and share a hotel room. It makes for quick re-fueling stops and potty breaks. It's easier to decide where to stop for grub and when to stop. Simple: "Matt, you wanna do this or that?".
Now let's say we're bringing along just one more person. Now you need three people to a hotel room, or two rooms. Now that's three bikes to worry about maintenance or mechanical problems. And probably the worst part: getting a decision made. Everybody has experienced this- Ask more than one person: "Do you want to stop here or there?" The answers you will likely get will be different, or worse yet you'll get "I don't care". That's no answer.
Now add an additional person, or perhaps our wives. Oh, Lord help us.
Aside from the quickly escalating number of 'non-decisions' we have the ultimate slowdowns for re-fueling or eating, or just taking pitstops. And on top of that, if we bring along wives, who is gonna take care of the kids back home? Locking them in the basement with pop-tarts, water and cable tv will only work for about 7-10 days. We need at least 14. Dang!

Dilemma #2 - Where are we going and how are we getting there?
The first part is easy. We've always had a goal. At first it was simply to Vancouver, British Columbia (thus, "Gordo's Vancouver Adventure", duh). But that evolved into "Vancouver with a side trip to Alaska on the way back." Again, still not a big deal.
The second question - how are we getting there?- is the toughie. Do we want to zoom out and meander back? Meander out and zoom back? See as many sights along the way as possible? Just get to the goal and get back? Scenic (but slower) route or superslab (and boring) route? Avoid big cities or cruise right through them? Want to complicate this further? See Dilemma #1 above. Add more people and watch the confusion come to a rolling boil. And this is pretty important for trying to plan overnight stops, and finding decent roads to travel that aren't torn up by construction or delayed by endless traffic. Plus, shouldn't this be a fun trip too?

Dilemma #3 - Getting attention
Since I wanted to make a splash about this trip, I need to get people's attention. Let's back up. I want to make a splash so that I can help out a charity that I feel is in need of attention (and money). You can't raise money for anything without getting people's attention. Time out: Technically you can: The only way to do that is to add on an additional tax to something and earmark the additional money for something (Governments are experts at doing this). Then you can pretty much do what you want and people will 'contribute' money without even knowing it.
I don't have that luxury, and I want people to know that they are making a positive difference. So I need to get people's attention to get at their wallets and billfolds and ask them to pony up some fundage for a good cause. Most people will give what they can. They do care, they just need a little prodding. (Yeah, try not to get a mental picture when you hear the words 'prodding' and think about Chron's Disease or Colitis. Ewww...gross.) So, back to the subject at hand: how to get attention?

The usual suspects: media releases, emails, social networks, and my favorite: bugging the hell out of the media. Keep at them until they do what you want just to shut you up. Keep calling the tv stations and newspaper editors until they stop taking your calls. It's just like being a vendor! (grrrr!)

Dilemma #4 - How much gear to take?
Neither Matt nor I have done anything like this before. How much mechanical gear (fix it stuff)? Bike fluids (extra brake fluid? oil? coolant? gas? filters? fuses?) How many days worth of clothing? Snacks? Laptop? battery chargers? Cold-weather gear? Hot-weather gear? How many pairs of shoes -or any? First Aid kit? Where the hell is all this stuff gonna fit? I don't want to be unsafe by being overloaded, and

I don't want to look like Jed Clampett, cruising down the road.

Dilemma #5 - How to Make Friends and generally not annoy people.
This is somewhat related to Dilemma #3 above. Certainly I want to share the news of this trip and the planning of it with my family and friends. And of course, using Facebook and other social networking sites, I have the opportunity to spread the news about this trip (and the raising money for charity stuff) with hundreds, if not thousands of people. But how to do so without irritating and annoying people? We all know that being Mr. Nice Guy seldom works. So I can take that route and ask nicely if people will share the news. Then when I still don't feel as though the work is spread enough I'll likely start spamming everybody I can find an email address for. Does it drop me down the same credibility level as a typical spammer? Almost. Is it worth it? Probably. Got any better ideas?