Look
here - down the the lower part of the first post for "Timed Feeders" for some chatter on them. I think they are worth their weight in gold for a diabetic cat. When I went back to work we had punkin always fed at +3 from the feeder, and if there was a lower preshot, then it fed him every 1/2 hr or so. You might consider getting 2 feeders and having them timed to open simulataneously. Put the same amount of food in both and unless Wrigley is really skittish he'd probably get to eat at least one of the feeders. It's pretty important for a diabetic cat to eat more than just once every 12 hrs. You don't want to overfeed them to the point they gain weight, but food is how you bring up low numbers, and if you're not there, the timed feeder substitutes for you in case he goes into low numbers.
If he is low in the morning at this stage, I'd probably just skip his shot. If you had data to show that he would just stay flat in greens, that would be different, but he hasn't been diabetic long enough for you to know that yet.
Also take a look at the top of the "stickies" - the posts that are fixed at the top of this page and the first one is on how to manage TR with a full-time job. It can be done - but honestly, i think skipping is part of the solution when your cat is newly diagnosed.
For the feeder - I'd take the amount you normally feed him in the morning and divide it into 3 portions or so. Feed him one portion with his shot. Set the timed feeder to go off at +2 and +4, and put the two remaining portions in those two slots. There's some tips about timed feeders in the post above that'll be helpful to you.
I did the same thing in the evening for punkin. He always got his +3 meals from the feeder.