Having done just what you are talking about - buying my first glider
and getting serious about XC and worrying about being frustrated with
my choice - I did buy a medium performance ship (DG-101G ELAN which is
factory spec'd at 39:1) and have been very happy with it. Why this
ship? It was considered good (not great) performance, easy-ish to
rig, not very expensive, one was available (an important issue), while
being fairly docile (spelled s-a-f-e-r).

After four seasons am I itching for a better ship? I would say yes
but not terribly strongly. I have flown the DG in a few contests
(sports class) and had a lot of fun. I got my silver and one leg of a
gold in it. Supership? No. Fun for an early XC pilot. YES. Having
your own personal ship (versus a club or rental ship) opens all sorts
of doors allowing you to fly when YOU want to and when the day is
good.

Now, here come the "BUTs"....

But, I work full time so my flying is limited to weekends typically.
But, if I was retired and being able to fly much more often it might
be a different matter for me. Meaning I would have a stronger desire
to move up.

Good luck. Have fun. Stay safe.

- John

PS We have two PW-5's on the field and the comments I hear from the
owners are; 1) very light weight and easy to rig 2) very light weight
and doesn't penetrate well into head winds. Can't have everything, I
suppose, unless you go carbon fiber.