How difficult is it in 2018 to transition from active duty to Guard/Reserves?

1LT (Join to see), where are you stationed? I see a lot of advice about the reserves and ARNG on here, but nothing that answers your primary question. Can you do it? The answer is yes, but it isn't likely. You signed a contract. Find it and read it. Doesn't matter if your Company Commander supports you or not. This depends on the requirements of your branch and your year group. If they are short officers, then the answer is likely going to be no. If not, then the answer is maybe. Your personal business is...not a factor. You're an officer in the Army of the United States. Period. You could be deployed tomorrow. So, I hope it works out for you, but you need to do some research and talk with the right people. I'd start with the ARNG recruiter and the Reserve recruiter on post. From there you can actually get some useful information. Anything is possible. Just depends on what your branch has to say about it. No one else can approve it.

I’d say the worst part of a drill weekend is the feeling of Groundhog Day. Running into the same problems each drill over and over.

Depends on needs of the service. If your job is not on a "hot list" you should be able to do it however the process can be long. You might find its better to just serve out your AD commitment.