In the back of my mind I was thinking about the tree thing, I know that dogs have used trees as a means to escape. The dog run might be a great idea to contain him when you're not watching. Put some thought into it though before you build. Most are made of chain link, but I'd highly recommend closing in the top too. Like I said escape artists are usually good at climbing and chain link is a walk in the park if you don't totally enclose it he could still get out and also the getting hung up problems especially apply to chain link. Also, unless you concrete the bottom or bury brick or steel cloth under ground around the edges he could still dig out.
Well, I've seen TV shows on Doggy Daycare, but never actually been to one. They seem to be pretty good, but I'd go in and ask for a tour (behind sceens too) and get a feel for the employees and the facility. As I mentioned about training, if any one or any thing makes you uncomfortable ask questions until you're satisfied or don't use the place. Be wary if they are vague about stuff or if they don't allow you access to certain parts of the facility. Most doggy daycares have play sessions, but I've never heard of one that offers training, not saying they don't exist, but I'd definately ask about the quality or level of training you can expect. Yeah, some people let others train their dogs, but I personally feel it better if you go through the training. As mentioned before, it's really owner training, meant to teach you how to handle, train, relate to your dog.
I use to work in a kennel where we had day boarders (babysit during the day while owner was at work) but we weren't set up like a doggy daycare because we mainly boarded dogs for longer periods so the day borders basically stayed in a single run and didn't get individual attention all day long. We would take them out to run around in a small play area or play with them in their runs, but that was about it. The daycare concept is good and is actually a lifesaver for many dog owners who would otherwise end up getting rid of the dog for behavioral reasons (separation anxiety, destructive chewing, escape atrists, etc.). I'd also recommend checking out more that one place so you have something to compare to.
