You could have a "starter" bike that is also a "keeper," like a street legal dirt bike (TW200, for example) - that way, you could have 2 bikes - one for messin' with on and off roads, in some wet or light snow, whatever, and as a backup for any time your bigger bike is in for maintenance, etc. Also, if you camp or want to take a small bike with you somewhere, you can do it with that small, "starter" bike.
I still have a Buell Blast, even though I now have 3 other 1200 cc bikes. And I still love to ride it. I'd surely take a hit on re-selling it, but what the heck - I've had fun with it up to now, and that's worth the price I've paid.