I see it as an opportunity to own a quality motorcycle for the price of a toy bike...
Yep. If you can find one.
Remember I'm 44 years old...
WTF??? I'm 47, but can't figure your meaning here? A certain age requires a certain bike?
...risk buying a last year model of a bike who's factory has been shuttered, probably permanently...
True, dat...
...I currently only have a KLR650, which doesn't get ridden much as it is really just a street bike capable of fire roads...
This tells me you already know what a KLR, DRZ, BMW F, etc. are all about and want something more aggressive like Husqvarna, KTM, Berg, Beta... Although, I've seen guys do some pretty gnarly stuff on KLRs.
I want a bike that is not just capable of riding up trails but also FROM trail to trail and designated riding area to area without having to look out for rangers/sheriffs/CHP. And if I feel like taking it easy, just ride the fire roads from Upper Lake over the mountain and not get hassled...
Your KLR will do that. This is where I get confused. You are "44 years old" and don't mention aggressive riding on tough trails/single track, so the need/desire for something more than a "toy bike" seems ill defined.
Unfortunately, I don't have much spare time in my life to devote to tinkering with hobbies.
But you want a high-strung dirt bike?
The lack of dealers is an issue. There just aren't any in my area, except for Monroe Motors and they are really a street only shop, so problems requiring dealer attention will take days out of my life.
Mail order is your friend, along with a shop manual, this site, and a good set of tools.
Also, the "get on it and ride" temperment of the lesser bikes is attractive to me.
Then you have your bike - KLR650. Perfect for a 44 year old guy who wants to ride to easy going trails without hassle on a bike that needs little attention.