I think one of the best bikes you can pick up for your budget is the Yamaha Diversion 600. There are some low mileage examples often advetised in MCN.
The Suzuki GS500 is another bike which can be cheap to buy used, as is the Yamaha Virago 535 - which has shaft drive.
With all these bikes you get a simple but very solid engine, easy to service as there are no rads and plumbing - less to go wrong.
Of the three I say try to get a Divvy. Quite a few of these were bought by the 'born agains' as their first 'big' bike, so if you can find one which has been used little by a mature owner, you are onto a winner!
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