This is a conversation I would rather have by a campfire. It looks like were both in So Cal so if we ever meet up on the trail I can give more details.
I have done/helped/assisted over a dozen engine swaps so far and diagnosed/helped diagnose even more. Each one had to meet Cali emissions. If I was going to do a diesel it would be the cummings 2.8. The nice part is their 50 state legal and the cummings shops are being trained to work on them as a conversion motor.
Now the bad part. When this is done you will own a Frankenstein. Cummings eng, advanced adapters "adapter", GM manual trans, advanced adapters transfer case. The GM 6 speed auto would be nice but it opens another can of worms.
Your not going to find anyone to do any real diagnostics outside of the engine itself. You will need to be the expert.
Next issue is making the other computers and gauges in the vehicle work properly. Custom mod's on the fuel system and tank and a bunch more. Most of the engine swaps I've seen over the years are sold within two years. I cant count the number of people who have come to me with weird issues after buying someone's "professionally" done swap.
Your estimate of around 30 grand is pretty realistic. I did the math on that motor into my FJ80 and came to around 25 grand with me doing all the work. If you found someone who has done several swaps into a discovery, your already ahead of the game. If not guess who's vehicle is their learning curve.
I'm not trying to badmouth or putdown anyone who may have done something like this. I know what it takes to do these things and they all look great from the outside. Alot of this hinges on what year the discovery is also. The newer it is, the more computers you need to trick into thinking it has the stock drive line. That is if you want to retain the factory features. Most of your high end computer vehicles have all the computers talking in a loop. Remove the engine computer and they don't know how to react.
My advice, if your going to do this, get a 1995 or older vehicle, gut it and make it a toy. Fewer computers and you don't have to worry about re-tuning that cummings to put out more power.
Sorry if this looks like a rant, it's not. Ive seen too many people over the years do things like this and not get what they thought they would end up with. I have also only touched on some of the challenges that need to be overcome.
As I said, in person I could do a better job of hitting all the high points and challenges. This was a swap I was going to do. The reason I didn't go farther with it was I decided to stay with the factory motor.
Scott