R1100GS and DR350SE
First off, I'm a cheap SOB, but hear me out.
I got tired of having to pass up dirt/gravel road adventures while riding my 1981 Honda CB900 dresser, so for 20 cents on the dollar ($4000) I bought a 1995 BMW R1100GS with 50K miles to serve as my "adventure" bike. It's my primary street/commuter bike, will cover long distances in complete comfort, and I can turn down any dirt/gravel road to see what is at the end of it. Did I mention it handles like a sport bike and what torque.......
Next, I was growing tired of loading up my 1985 Yamaha YZ490 MXer in the back of my truck and hauling it 1-2 hours to a place to ride it. At 52 years of age, I was getting tired of kicking the beast to start it too. I decided to replace it with a nice 1995 Suzuki DR350SE ($1200) that came with a license plate, electric start, resonable weight, and is air cooled (can you say simple). It ain't no race bike, but it serves as my dirtbike and can be ridden on the street too.
For me there is no one bike that will cover all of my biking needs, but these two cover 95% of them and the combined cost was less than a new KLR.
Of course, there are costs associated with purchasing used bikes, but you can find great buys if you are patient and I don't pay the 30% depreciation of a new bike when you drive it out of the showroom.
Did I mention I'm a cheap SOB.........