haha, great pictures. He actually reminds me a lot of wally with his stripes! I can tell you our experience with crating and you can take what you want from it:
When we got wally at 10 weeks, we were very strict about putting him in his crate at night. During the day we did what others mentioned and put treats and toys in the crate to encourage him to go in there. We also, however, let him nap on the couch which made it a bit tougher at night to get him in the crate. At first we would put him in there and have to stay with him for about 20 minutes until he calmed down and went to sleep and then sneak away to bed. He would then generally sleep until about 4 or 5 am and we would take him out. Our (my) problem was that once he was in the crate, that was it. Any noise woke him and he would whine. I tend to be a night owl so it was very difficult.
Right around when he turned 5 or 6 months old we decided to let him sleep in the bed to see how it went and we've never really looked back. To us the negatives have been greatly outweighed by the positives. I'm out of town 4 nights a week and it seemed silly for my wife to have to spend time trying to get him in his crate at night and then sneak around the house so as not to wake him. He now sleeps in as long as she does, there is no getting up at 7am to see if he needs to go outside. He will basically just stay in bed until we forcibly carry him out of it. To us, it was really nice just having him in the room with us and not worrying about whether he was whining, sleeping, peeing, whatever. He has never had an accident in the bed.
Our other reasoning was that we keep him in the crate during the day when we're not there (with walks every 4 hours) and hated coming home, taking him out of the crate and then putting him right back in at bed time.
So, basically, having a dog sleep in bed with you may not work for some but it has worked for us. The good part is that it has had no impact on crating him during the day. We have never once heard him whine in the crate during the day. He only does it if he knows we're there, otherwise he gets in there and doesn't even play, he just goes right to sleep.
Sorry for the long post, but i hope this helps. I kind of feel for you guys as the first several weeks were TOUGH! Hang in there though.