My current bike is Honda NT700V Deauville that I bought brand new in July 2011, with topcase installed. It still needs some updates, but I hope this is going to be as enjoyable relationship as we had with the Old Lady.
My previous bike was a second-hand Yamaha Virago 750, 1991 vintage, that I bought back in 1996. Got it with aftermarket pipes (somebody said that they were Jardine Slashcuts, but I think they actually were Cobra's) installed by previous owner (probably rejetted too) and only 4500 miles on it. It was in very good condition missing only a chrome cap from the right grip and half of chromed plastic lining from front mudguard.
During the 15 years that it served me well I replaced the grips with 'foam' custom-look ones, front springs with Progressive's, and bought a new seat from Mike Corbin. I also added a XV1100 style sissy bar, engine guards and a small shield. Also hacked together a cigarette lighter brancet that was bolted to the frame where XV1100 has fuel pump.
Other than oil changes the only think that broke on it was gaskets on one front fork tube when I went over a bump on a road somewhere in Sweden on my way back from one of the several Norway trips that I made with it. Yes, it had a chronic Virago started disease but this did not improve or worsen over time, so I just lived with it.