OK, just to stoke some controversy, I'll add a contrary opinion:

There are two questions: What first glider to own, and what cheap
glider to own. These are often confused.

Unlike in many other sports the "latest and greatest" does not take
any more skill or finesse than older gliders. If you have the money,
there is no reason at all not to make your local dealer immensely
happy by ordering a modern glider, or buying one of the many excellent
used ones for sale. If you are qualified to fly a Libelle, Cirrus, or
PIK, you're qualified to fly a 27-28-29, or D2/V2.

You get easier handling and a considerable improvement in safety. All
the new gliders have better balanced controls. Winglets make a big
difference in thermals. Spin prone tips, all flying tails, small
slippery airbrakes and all that got sorted out in the 80s. The "safety
cockpit" concept really didn't begin until the late 80s and early 90s.
You also get a trailer that is much much better than earlier models.
Landing my ASW27 is much easier than landing a libelle.

(Of course new pilots should stay away from open class, tricky
gliders, and motors. Power pilots should absolutely not get a glider
with a motor in it -- they always seem to want that.)

Older gliders are lovely. Old cars are lovely. But old anything means
lots more care and maintenance. Nobody said the three most important
things to look at in an older glider: Gelcoat, Gelcoat, Gelcoat. It's
only a matter of time before that $15,000 + bill comes due. Plus rust
on the fittings, ADs, bags that leak, fittings that break, bearings
that wear out, manufacturers who don't exist/don't stock older parts,
and so on and so forth. It's a tradeoff -- save money initially, but
you will invest more time. If you don't know how to do it yourself,
you'll invest lots more repair money down the road too. If that's for
you, good. If you have the money and would rather spend time flying,
do it.

I have to disagree pretty hard with the advice here that KA6s and the
like are good gliders for new pilots to consider. KA6s are beautiful,
fragile, wooden antiques. They need lots of expert tender loving care.
It's like owning and driving a Ford Model A. Vintage and antique
flying are wonderful hobbies -- but not for a new pilot with limited
time and expertise at glider maintenance, whose main interest is in
flying.

Plus, look hard at the bottom of a KA6. It looks like a gorgeously
made wooden boat from the 1950s. Now think of your butt down there,
crashing in to something. Splinters are not a safety cockpit. When you
go for gliders this old, you're making a big tradeoff in money for
safety. Now, that's probably ok if you want to float around the
airport and enjoy your beautiful antique. Missing seatbelts are ok for
tooling around in your Ford Model A on a sunday afternoon. But if you
want to push the cross country or contest envelope, it's a much more
important consideration.

This post started with "under 20k". But where did that money limit
come from? Maybe that $20k limit isn't so hard and fast after all? I
bet it came from a perception that the cost/value tradeoff peaks at
$20k. I hope the above makes you look a little deeper.

Here's how to explain it to the spouse. Don't look at the list price
-- look at the annual cost. Gliders don't depreciate. If you buy a
glider for $20k, you'll sell it for $20k a few years from now. So a
$20k glider is really costing you the interest you'd be earning each
year. That's maybe 2 percent per year right now, so a $20k glider only
costs you $400 per year! Even if you have to borrow, home equity
loans are about 5% right now, so that $20k glider only costs $1000 per
year. The insurance and tows are going to cost more than that!

Maybe a $40k glider, meaning $800 lost interest or $2000/ year
interest cost, isn't that "expensive" after all. And with a partner
(an excellent idea for a first purchase) now we can talk about an $80k
glider! Owning a glider is, in the end, pretty cheap. Try to play
golf or go skiing on $2000 per year! (No, I'm not on the dealer
payroll!)

It is also a bad idea to buy a glider that you know you'll outgrow in
a few years. There's a lot of pain in the butt with buying and selling
gliders, setting up instruments, paying sales taxes, and so on. Spend
a bit more now, and be sure you'll be happy with it for at least 5
years. The difference in performance of the new gliders is pretty big.
That doesn't just mean you go faster, it means you stay up and go
places others can't. That "'cheap" glider will end up costing a lot if
you dump it in a year or two because you're tired of watching your
buddies go places you can't.

John Cochrane