Would appreciate some advice on buying my first bike.

Thank you everyone for even more great replies! WR250Rs and DRZ400s are definitely growing on me. Found a really nice DRZ400 in my area. I'm not sure if outside links are allowed here? But this is it. http://vancouver.en.craigslist.ca/pml/mcy/4323472279.html

I realize its a SM. But I've read thats it's better to start with a SM and get some spare knobblies than it is to start with an S and get spare street tyres. Is this true?

The guy is asking too much and he knows it... Also he is looking for a big dual sport or a daily driver. I would never recommend ridding those off road , they don't do good . Even with wheels it's still a street bike with street bike suspension. A DRZ 650 is still my advice. And no it's better to start with the S because the S crosses over to street better than the SM crosses over to dirt.

Sounds like you are getting some top notch advise.
Another thing to consider is that the only Huskys that have a gear box that is highway friendly for more than a few miles are the 610s,630s and TR650s. The 610s have an excellent 6 speed, don't weigh very much more than the WR250s and much lighter than the DR650s.
Unless there is a dealership on your island all the parts you will be needing will need to be ordered.
I have a 30" inseam and can flat foot my 610 with a Seat Concepts low seat.
There are a lot of great bikes out there.
Good luck!

My island has 280 population xD If i want to get chicken, or beer... Gotta take a ferry... So I'm not to concerned about having to order parts, or travelling for them. However I think I am going to wait to get a husky now. Get a bit of experience under my belt with something I won't care about dropping. DR650 and DRZ400 are at the top of my list currently. Everything seems to be pretty expensive around my area though, and there aren't any Suzuki dealers within a couple hundred miles. My best options would appear to be either this DRZ400 http://vancouver.en.craigslist.ca/rds/mcy/4374887546.html or this DR650 http://vancouver.en.craigslist.ca/rds/mcy/4388529571.html Im going to go take a look at them both on thursday and see which one I like the feel of more. Other than looking at the sprocket and chain for wear, and fluid leaks, what should I specifically be looking for?

I agree, that's too much for the DRZ400, and an SM is not really what you are looking for. Any enduro bike with a good set of tires like the; Metzeler Enduro 3 Sahara will be perfect for what you are looking for. The WR250 is a great bike, and so it the DRZ400. A Honda XR650 would be good too. Like others have said, low maintenance intervals and parts availability are important considerations. Regardless of your choice, welcome to the world of motorcycles. Be careful, stay aware and have fun.

Oh, ask about riding gear (helmet, boots, armor, etc) next. There's so much to discuss....