One thing I really failed on as a pet parent and trainer was crate training... lol. Jackson was terrible - he whined and yelled and barked and would NOT stop (if I was home with him, and tried to crate him) so I ended up just giving it. Luckily when I got him I had a lot of time as I was off for college break so was capable of watching him all the time, and being sure he did not have accidents. Thankfully he proved himself to be very reliable quickly, and by 6 months old, he had basic full run of the house (minus the upstairs). He also began sleeping in my bed around 15 weeks old and has been there ever since
But yes I would start by making the kennel a positive experience. Check out Kikopup on YouTube - she has some great videos on training including crating. Here's one: