I used to have a Caddy, sold it around a year ago.
A straight Caddy with no engine is a better investment than a wavey Caddy thats mechanically sound. The one I had was wavey but mechanically sound and there is just no point in sorting out all the dents so it stayed as a bit of a ratter.
Things to look for:
RUST! As it's a pickup they were bought by farmers and around 7-8 years ago were worth nothing so they were not looked after.
RUST! Lower areas of front slam panel, wings, doors, front of rear wheel arches - use a screwdriver to poke here, Windscreen and rear bubble screen surround and of course the bed (if you spend £2000 you might get one with no patches on it, haha)
Cills/Sills, however that is spelt, as with mk1 golf they are often thin and rust from within, could have taken a pounding from going off road.
Sagging/soft rear leaf springs from carrying weight. Replacement springs are not easy to find and can cost ££'s for new ones. Check wishbone bushes and mounting points because they can perish and mounts rust apart.
Tailgate, make sure mechanism is working, if mechanism has come apart you may have to cut open the tailagte to sort it= hassle! They are bananad if they have had weight sliding back against them. I decent tailgate can easily cost £200+
If it's original and not been looked after expect to replace all wheel bearings, front discs & pads, ball joints & wishbone bushes.
Check whole underside of truck, it will have been off road and the underneath takes a battering.
Dodgy wiring, wiring to rear lights is sometimes dodgy
Anything that is an issue with a mk1 golf will be an issue with a Caddy
Engine wise the 1.6d is slow but you get 45mpg. 1.6 carb is a bit quicker but not as eco. Caddy sport has a 1.8 gti engine but you will pay 4k+ for a good one. 1.6's are 4sp but can easily be sorted by throwing another engine in.
Join mk1caddy forum, always loads for sale and they are going for fairly good prices at the mo due to people having to sell off unfinished projects.
Good luck! over and out.......