Well, to answer your first question, e.

I enjoy riding a bike. But with everything else in the world, variety is the spice of life so I like old, new and everything in between. Doing the same thing over and over again is not for me. And I can afford a quality modern bike and a quality classic bike. I don't need to choose. What I won't do is own 2 bikes from a similar era as it does not add much to the variety I enjoy. Disclaimer - I'm no princess and cannot discern subtleties like a centimeter in trail difference, a degree in seat tube or head tube or different tubing types.

Now if I had to choose 1 single bike to ride until the end of my days, I'd choose my 1933 Frejus if I stayed in Illinois and the 2009 Cinelli if I moved to somewhere with significant hills.