Hi Kevin! Glad to hear you're making progress!

One of the strategies we've used on our pup, Link, is feeding his meals in the crate. The food would be his kibble, mixed with just a little bit of water, filled in a Kong and then we freeze it. When it's time to feed him, we would put a little bit of peanut butter on the Kong so he licks at it, which gives the kibble time to melt inside. This increases the amount of time he has to work to get the food and also spend in the crate. While he'd work on the Kong, we would praise him and just cheer him on so he has a lot of happy feelings/associations with the crate. (We got the idea from Simpawtico Dog Training)

We've been doing that for several weeks and he's definitely more comfortable going int and out of the crate. An occasional whimper but he usually calms himself down after a few minutes; we also include a few Nylabones in the crate for him to chew on.

It's such a great feeling when you see them going in without fear. You guys are doing great! Just takes time.