Hates his leash

I would definitely keep using the food or a really good treat when desensitizing him to his harness. But when it comes to the harness make him work just as hard as you do when you're practicing your recall. Keep him on one side of the harness and the food on the other and make him put his head through the hole before giving him the reward. He's going to want that harness on him a lot more if it means getting food to do it! You may be inadvertently encouraging him to fight by giving him the food when he's fighting you or moving his head away. You want him to see that harness and think 'FOOD!'
 
I just needed to let you all know that Romeo's making great progress! Maybe it's the new freeze dried beef liver treats that I'm using now but putting a collar and leash on him no longer requires me to run a marathon chasing him first!

I did as k9kreationz suggested and dangled the collar in front of him (adjusted so that it's a huge circle that his head can go through) and held a treat on the other side of the hole. It took 2 secs for his head to go right through, no effort on my part! haha! Then I tightened the collar as he happily munched on the treat. SCORE!

I don't know what prompted the change, but he now runs to sit by his toy box which also holds his collar and leash whenever I put on my dog-walking waistpouch (signalling his evening walk). It's like suddenly he really likes/looks forward to the part before the walk! The part where I put on his collar and leash! haha! My boy is so weird.
 
My sheltie also hated his leash. I tried everything from a normal collar to the pinch collars but he didn't like any of them. So I bought a leash like they use at the vets office for $1.79 online and he doesn't seem to mind it at all. I'm thinking he didn't like the way the collars felt around his neck.
 
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