Originally Posted by WestVirginia
As a college graduation gift I bought myself a Yamaha dual sport 250. Great fun, no maintenance due to low miles, but always felt "naked" on the highway. Sold it after about a year or two when I moved just outside Washington DC. You'd be surprised at how few off road trails there are in D.C.
My 2 cents.
Going from a 20 year old (with a 20 year gap) 250 to a Tenere seems like a HUGE jump to me.
Learning moto maintenance on a carburated, chain drive, tubed tire non-ABS bike so that you know how to work on a FI, shaft drive, tubeless ABS bike seems a bit odd. I think the only maintenance items that are similar would be fluid changes and checking the tire pressure.
Start with a used Wee. It's fast enough for now, and so much better than a KLR on fast pavement. If you buy it used, you can ride it for a year and sell it for the same money (this works well if you decide to get a faster bike, or decide bikes aren't for you).
I've never quite understood the "I want to get into motorcycling, so I'm going to buy a $15,000 bike" mentality. On the other hand, I want to thank the people who buy nice things, take care of them, and sell them to me at less than half price a few years later. Perhaps you have a financial situation where none of this matters.
In any case, have fun and ride safe.