I believe the tradition of customizing cars and the culture around it is somewhat different in the US and Europe, being complimentary to each other and not neccessarily countradictive. As far as I understand Singer, the base cars tend to be (or close to be) beyond rescue, and they provide the joy of driving capablilites whilst caretaking the vibe, which is just as important. The vibe isn't always there with modern cars.
My take is: Go ahead and give owners the feel they search for, but stay away from unique and rare cars of historical value/importance. They started off with 356 I believe, and if there are a healthy number of original good cars preserving historic value, they can knock themselves out with the rest
There is a somewhat similar thing happening to old jags, and with the culture around those, I believe it contains a bit more controversy, but again, if there are enough cars caretaking the historical aspect, it's fine in my book.
Then: Who wouldn't love to own and drive a classic beauty, be it 356/911 or XK150/E-type or a Daimler double six with actual proper roadhandling? I know I would
As for the Singer watches, I picture those more like a take with a twist or two on an exisiting trend, the standout piece would be the Divetrack. The Singer Reimagined watches are not really my thing, I empathize more with what Omega has done with cal 321.
With the cars, Singer takes vintage/historical objects and enhances them, adding to the history of those cars. With Singer Reimagined they take old stock movements (am I right?) refines them (and I'm sure there are benefits added in not only decoration/finish, but also performance), and mount the movements into their own creation. Not sure, but I feel there is a crack in it somewhere which differs from their car approach, which is rooted both in the cars and even more so, rooted in American custom car tradition.
Does that make sense?