I can't comment on the diesel, but the Grand Cherokee is a great towing platform for a boat. I had an 07 Hemi that did a great job pulling my 5000 pound 21' boat. The only downside was 10 MPG with a smaller fuel tank made frequent stops. The 3.0 CRD would get significantly better MPG with similar towing capability, so my main complaint probably would not apply to your situation.
If you read FishOn's other posts, you will notice a severe bias against any Chrysler product. Make sure you take that into account before taking his post as gospel. A better question may be would the CRD resale value stay that high if parts/service really was a problem?
