I just made the mistake of stumbling back into this thread and am disappointed. Not surprised, but disappointed. Many of you (ThumperX, Flying Hun, Ezekial and others) have made sense. Then there's the "must ride a 250 locally for 6 years until you should even consider crossing the state line" crowd. Wow. Just wow.
A bit of local experience would be well-advised for a couple of reasons. It would allow the new rider to become comfortable with some of the basics of riding in traffic, and it would also be a good shake down period for the bike. The latter is a good idea for any used bike, as it is much better to have something unexpected happen close to home, and something unexpected is likely more likely to occur shortly after purchase of the used bike than it is after it has been ridden a bit (on a per mile basis, for those who want to get technical).
There are a great many bikes which suit beginning riders very well and, believe it or not, some of them even have more than 250 cc.

Power delivery on an SV650, for instance, is going to be perfectly manageable for all but the most ham-fisted of riders. It will also be better on the freeway than a lighter, lower displacement bike. The SV was just an example, but there are dozens, if not hundreds, of bikes out there that are solid, beginner-friendly rides.
I'll stop before I ramble-on into TLDR land.