He looks lovely before and after Charlene but I know how upsetting it can be if they have a cut you are not happy with, my 2 always have all their feathers and skirts etc as much of a show look as I can achieve, but they had an incident with Gloss paint 10 mths ago and they were both completely shaved, Belle looked like a lab pup and Monty looked like a little Great Dane, to say I was devastated was an understatement, BUT within 6 mths they were more or less back to their old selves, and now you would never know
I think you will be able to trim Diesel by yourself, Cockers seem to fall into catergories when it comes to coat, the darker blues and Blacks tend to have more difficult thicker coats, and the lighter shades tend to be easier to manage, Diesel has a lighter coat and for his age in the before pics doesn't look profuse at all, you should have seen Belle (black) at 5 mths
Monty my Golden/Red has a much easier slow growing coat that looks much like Diesels and is easy to manage. Get him used to the table lots iof treats annd a little comb through a couple of minutes a day so he sees the table as somewhere he will get treats and then slowly work up from there, we have all made mistakes but don't worry it does grow back.
I would a comb with an elastic band to get out his puppy fluff, good luck
Jo