Ideally, you want an older bike that has a good rep and can be had for cheap (to buy and insure).
That way, you get some decent use out of it and it will hold it's (meagre) value.
Plus, if you accidentally drop it (as many, but not all, new riders tend to at some point), it will be cheap to fix. If something worse happens, you won't lose too much on it either.
I'd suggest something like a Yamaha Diversion - 600 (chain) or 900 (shaft). Pretty solid, ticks all the boxes above, easy to ride, mileage is not a concern and while they can easily be found for under a grand, they sell for the same as well (or more, if you tart them up a bit)!