I agree, make him an indoor dog! Or at least outdoor partially & not completely. I see you live in Utah. Its Cold there!
Bring him in! I'm not telling you how to live your life - but Cockers are very much people dogs, and need to be around people!
They are very much "velcro dogs". We all say that around here, and we have a reason for it - they are constantly at your feet,
and they like it that way. I do too, TBH! Keeps him out of trouble...well most of the time.
I also agree with Dani, get him shaved down ; if he hasn't been groomed in 2 years ; I bet he is a mess. Find a groomer to do this.
Its NOT going to be easy if you do it yourself, because if i was betting he is going to have skin issues & put up a real fight ; and both you
and the dog will just end up frustrated. No point in it. After shaving him down, if you still want to groom him yourself purchase the Zims
Grooming DVD. Jim has a link to it on his
Grooming Page. It has a list of different
grooming materials you will need such as a Nice pair of Clippers, Oil for the Clippers, Two-Sided Brush, & Grooming Table. I just invested
in a Grooming table - I didn't have the money to purchase it before, and I got it for Christmas! Its VERY helpful, thats for sure.
If you start to brush the dog out everyday or 4-6 days out of the week; it will get better. He will learn to like being brushed, grooming may
take a while ; some dogs handle it better then others. Rudy is AWESOME. He doesn't put up a fight at all, expect bath time! He runs to the couch ; and turns into a log!

But, Grooming he is perfect, we started at a young age.
If you can't keep up with his Grooming & Keeping him Indoors, I would also agree with Dani & Debbie when they say Cockers may not
be the breed for you, they are very high maintenance, IMO; Grooming, Training, Attention, etc. They are beautiful dogs; but not for
everyone, thats for sure!

Maybe consider re-homing him to someone who has the time, talk with local rescues; but please don't drop him at a shelter, if all possible. I hope this doesn't come off offensive, I'm just giving you my honest opinion. Good luck.