I'm retired wildlife director (KY). In fact I worked for your wildlife agency for 11 years and still have frequent contact with folks in the IDNR. If you will PM me I'd be willing to carry your case directly to the Director of Wildlife and the Director of Law Enforcment for you.
There is a lot of good, legal advice in this thread. I can appreciate how very frustrating this would be.
I would not want to spend my valuable hunting time staking this fellow out. Neither would I want to degrade deer hunting on my property to try to keep deer from this fellow's hunting zone. This is very difficult to do and could actually backfire -- an anti-hunter once drove a nice buck under my treestand trying to scare the deer into Potato Creek State Park (no hunting). I obliged the anti by taking the buck home with me -- thank-you very much!
Neither would I want to damage habitat on my property to discourage this guy. It takes a long time to grow trees. Anyway, if you create early succession habitat (undergrowth) by removing trees and opening up your property edge, MORE deer would spend time near his hunting stand.
Your first attempt was perfect -- pictures to the CO. If the pictures weren't clear enough, get better ones -- as you plan to do.
That this fellow is a Hunter Education instructor is important. I would definitely report his activity to Tim Beck, one of Indiana's Hunter Education Coordinators. If Tim knows him, pressure to behave could be applied. Again, I will do this for you if you PM me.
Finally, the first thing I would do is let the fellow know you are aware of his illegal and unethical behavior. Let him know you will take pictures (he doesn't know the quality of your pictures) to the Wildlife, Enforcment, and Hunter Education Director if he doesn't agree to follow the law he preaches.
Be prepared, a fine citizen like this might not care if his Hunter Education credentials are taken from him.
If I didn't get satisfaction with any of these things. I might consider adopting a fine mutt. Then I'd stake the hound with humane cover, food and water in the vicinity of this fellow's tree stand. I'd guard the dog with a hidden camera in case he decides to kill it - then he's in a heap more trouble! The dog will be very effective in keeping deer away from the fellow's area. Of course if this area is good hunting and you don't mind sitting up in the same area, compete with him and watch over his actions. Especially if the times he hunts are predictable such as opening days.