4k out the door? To me.. that sounds like nearly new pricing.
I'd say your chances of getting a newer 250R for $2500 OTD is slim to none.

Ok, Ok.. so you've all made it clear that I'm way off and that the advice that my buddies gave is out of date. What's realistic then? 4k out the door? To me.. that sounds like nearly new pricing.
What we've been saying. To save your pennies and buy a used private-party starter bike that might not be as cool-looking outright, for less money.$2500 in hand will cover you for sure, if you're patient.

....
Sure.. you can find the occasional deal. But, you'd have to act quick and pounce with cash in hand.
you mean a honda rebel 250? or do they make shadow 250's?
you mean a honda rebel 250? or do they make shadow 250's?
You'll have an easier time getting a great deal on a bike that isn't in high demand.
An old friend started on an EX500. Great starter bike for under $2k used.
Good luck.
So you're pretty much stuck if it's not right for you, or it breaks.
There is no rule that you 'have' to drop your bike.
As far as dealer pricing goes, I've been watching the J&M Motorsports thread on BARF, and some of their bikes seem to be priced spot on, and others seem really high. I'm not sure what formula they use, but it seems like it isn't 1005 consistent from bike to bike.