Take a look at the new VStrom 1050XT, I love the retro styling.
That's the problem with working, all the money, no time to use it. I'd say go for it if you've got the money now, you might look back later in life and regret not doing it.
You can pick up brand new Royal Enfield Himalayan's for a few grand, dirt cheap. Not the fastest, 411cc single long stroke thumper, torquey but similar power to a 250cc. They're great for off-roading, a woman called ItchyBoots on YouTube has practically gone around the world on one.