As the OP doubless knows - these boats are more similar than they are different. Both about 25 ton loaded for cruising. Neither has daggerboards. I don't know much about the Privilege other than it has a fine reputation. I know the Leopard a good bit better.
The Leopard has a happy and passionate owner base who regularly buy a 2nd and 3rd Leopard. Happy Together is the owners' 2nd Leapord. This says a lot about quality and after sale
support. It's unusual to see someone buy twice from the same builder
The Leopard low price is partly due to the limited range of options (lower labor rates in South Africa
are a bigger reason). But private customers (e.g. non-charter) all customize their boats post delivery
. In the US, Just Cats is right next door to the Leapord offices. They do very fine work. If you want to re-arrange the interior
, just ask. By the time an owner finishes with Just Cats I suspect the gap between the Leopard price and and Privilege price has narrowed considerably.
When you start lifting hatches on the Leopard you find a very tough and sound boat. An example is that the steering
system is overbuilt -- and it is a traditional chain and wire instead of the hydraulic steering
you find in most cruising cats (not sure what the Privilege has). There is no slop in the Leopard steering
. Feels like a racing
And as mentioned, Leopard has a very strong worldwide warranty program. There are so many Leopards built that you can find people who know how to fix them just about everywhere - including every Moorings base (Leapord, Moorings, and Sunsail are all owned by the same parent).
While the OP didn't ask, I feel the need to raise a few concerns:
a) While both of these boats can circumnavigate safely you should pick your season and weather. While many Leopards are still delivered on their own bottoms they (and the Privilege) spend much more time hopping around the Caribbean
not crossing the North Atlantic in winter.
b) I had a good friend who bought a 55ft cat with the intention of taking his family
sailing for a few years. The whole plan fell apart when his 6 year old daughter had a serious seasickness problem. The whole plan fell apart.
c) What size boat does the OP have now? It is becoming very hard to get insurance
for a big cat unless you can point to years of experience owning a similar size boat. They frequently will require a captain