I think that Honda Shadow is nice for the price. And it shouldn’t be that much more than the 250 control wise. Yes the weight “may” be an issue but I think you can handle it. Of course I say that with a grain of salt. Take the MSF and figure out what you can handle in the beginning.
Then again $2500 is a great price and more so its a used bike so dropping it will not be as bad if you dropped a brand new bike. Personally, I would snatch that Honda up for that price. They are indeed great starter bikes.