Who seems to be, as before, charmingly indecisive about a bike purchase.
Seems like he wants a reliable and charming bike that will do smooth, rough, long distance, loads.
I think my 1990 Specialized Sirrus Triple would do the job. It's been carefully pre-patinated, and it rides like a magic carpet.
I could stretch to reach and fit his 1500 budget
(But the brooks would double)