I think you're going to have to choose between the AWD and Diesel or Diesel and Manual Transmission.
I thought my choice was between MT + AWD (= Subaru) OR Diesel + MT (=Golf Wagon)
(What is the least expensive AWD and Diesel 5 seater?)
Audi Q5 or VW Touareg - you'd have to check. One of these from the CPO program would fit 2 requirements out of 3 and your budget. The most recent awd diesel with manual is probably a 20 y.o. Land Cruiser as someone already posted.
Manual + awd + 5 seats is already pretty rare: Jeep (Compass, Patriot, Wrangler Unlimited), Subaru (all 4-pots), MINI (Countryman S), Audi (S4 and a selected few others), and I'm not even sure if BMW still offers xDrive with 3 pedals.
The only perfect match would be the new VW wagon, IF 4Motion is available, AND if they make it available with a stick - to date, all NA 4Motions are automatics. If the MINI Countryman moves to the turbo 3 with awd, that'd be pretty frugal.