I just gave my son my first NEW bike. A 2002 VTX retro. A bit over fifty K on the clock. But the bike I wish I still had was my 1980 Honda CB900 Customs. I had two of them. One to ride and one for parts. I loved the air shocks front and rear and the dual range transmission. Ran like a scalsed cat too.
My first street bike was a 1985 Suzuki GS550L. I rode the snot out of that bike for 11 years and I wish I could get it back. It wasn't too big and it wasn't too small. Today, there is no way that my oversized body would look right on that bike, but it would be nice to have it back.