Am I being silly in putting automatic connection so high on my list?
It just seems sensible to me and perhaps something that would make the
ship more marketable when I decide to move on or out in a few years.


No you're not! One of the reasons I upgraded from an ASW-20 to a
Discus 2 was for the automatic connections.

With the constraints you have, I think you should take a good look at
the 304CZ. I nearly bought one myself and can testify the handling is
very good. Being a newer ship, you won't have to worry about
refinishing and it should come with modern instruments and a decent
trailer (things you don't mention, but which I think are important).
With the 17-meter wings, it should be a good match for your east-coast
conditions. Its performance isn't far shy of that of the ASW-20.

Overall, German-built gliders have more brand equity than those from
other countries, but the 304 CZ has a loyal following in the USA and
used ones seem to hold their price and sell quickly.

Mike