1. You run the chance of making his association with the crate even worse if you decide to use a bark collar at the same time.
2. If determined, dogs can break out of those as well and risk injuring themselves in the process (with either crates).
3. Good idea..you can also feed him his meals in his crate by stuffing Kongs with his food and some peanut butter or canned food (freezing makes them last longer).
4. Off-leash play, walks, games, and training for a total of 1 1/2 hours is fine....1 1/2 hours of running on leash or alongside a bike is way too hard on his growing bones and joints.
I strongly recommend you read the book,
I'll Be Home Soon by
Patricia McConnell (make sure to lend it to your trainer when your done)
http://www.dogwise.com/itemdetails.cfm?ID=DTB667 and
Crate Games by
Susan Garrett http://www.dogwise.com/itemdetails.cfm?ID=DTA287 .
I think your main focus at this point is to accustom your pup to the crate. The only way to be successful at it is by having him associate it with both fun and relaxation.
I've recently read that melatonin may help with separation anxiety issues (while working on de-sensitization at the same time)...you ought to speak to your vet about it. Good luck
.