1. My fair share of riding will be around the streets and maybe a few times a year I will hit up some tame dirt roads. From what I read here, as long as I do not attempt serious off-roading I am ok right? I don't plan on making this the sole objective of the bike, just maybe a once a year thing job permitting.
Once you get this thing on dirt roads, it's likely you'll want to do it more than once a year.
2. I don't want to start a flame war, but it also seems like I would want to look for at least a 2007 model and if possible a 2008 to get the alternator upgrade.
3. I plan to buy a Wee used from Craigslist. Around the Chicago area, these bikes are not too common. I hope listings improve as the temperatures go up!
Keep an eye on the listings on this site and advrider.com as well. You'll see some good deals, I'm sure. And because those ads are targeted at a knowledgeable audience, the prices are usually fair.
4. I am 5'10" tall and although the dealer by me did not have any Vstroms on the lot, I sat on a Versys and a KLR650 for comparison purposes. The Versys was perfect seating height, but with the KLR it was awkwardly high. I barely kept the bike level with my tip-toes!
Someone correct me if I'm wrong, but I believe the Wee is a bit higher than the Versys. It's been a while since I sat on one. Still, if you've got a 30" inseam or better then you should have no problem. Many people like to lower the front of the Strom for the positive effects it has on handling anyway. The bonus side-effect of this is the lower seating position. That adjustment is widely known as one of the best cost-free modifications, and it only takes about five minutes to do. There are also lowering links available for the back if you really need them. They're pretty affordable
5. The cruiser had a really laid back seating position which was very comfortable on the highway. Is the standard seating position on the Wee just as good?
I think the C-50 had an upgraded seat over my Marauder. The seat on the Marauder was hell on the coccyx, but the upright seating position as compared to many other cruisers is pretty nice. Still, the more "proper" posture of the strom is far more comfortable, IMO.
6. What are the first items I should look to get on the bike? I am thinking that if they are not there yet: centerstand (invaluable on my vintage bikes!), crashbars and handguards (just for looks :mrgreen: ).
These are choices only you can make, but I'll throw in my $.02. I don't have a centerstand, but that's absolutely next on the list for me. My crashbars have paid for themselves three times over, and not because I do any rough off-road riding. I've laid the bike down twice in my driveway. With a bike this tall and top-heavy, low speed drops are common; crashbars make that okay. My handguards have only been of any consequence in cold/wet weather. If I had to do it all over again, the forkbrace and bar risers would have been the first additions after the crashbars. That's just me though. Poke around the site here and you'll find a ton of great info on accessories. This is one of my favorite threads on that topic.
7. If the buyer of my cruiser does not want my current soft saddlebags, are they compatible with Wee? They are Kuryakyn GranThrowover bags. Do I need to get some sort of "saddlebag stays" for them?
Those look like they may work. They can rest directly on the exhaust shield on the right side, but you'll need some kind of bracket to keep them out of the wheel on the left. Many have made their own out of a simple piece of aluminum stock. I've got Dan Vessel's luggage guard and love it for my soft bags.
Sorry for the multitude of Q's. Thanks in advance!!!