Agree with
@DeltaDogs - do not let your DS worry about learning to use starch or how to shine his shoes. The cadre have set learning objectives the swabs are required to meet from week to week, uniform preparation and appearance is a large part of that in the first couple of weeks. I'm a child of a two career military parents - didn't touch a shoe shining kit until swab summer and I did just fine. It's not rocket science - if your DS met the requirements to be admitted, he will certainly be able to figure out these minor things with the help of his cadre and classmates. (Note: If he does struggle, this is where prior enlisted and prior CGAS classmates come in handy!)
As for numbers 3 and 4 - your DS should sign up for a sponsor family if he feels it will be good for him. I ended up signing up for one, they were extremely nice people but I really only maintained a relationship with them my 4/c year. After that, I really just used weekends to spend time with friends, get homework done, and travel (both w/ CGA and on my own with friends). One of my friends had a great relationship with her sponsor family and I believe they're still in touch. It all depends. As to making friends with classmates who are local, do so if you actually click with them as people - if you do, there's a high possibility you'll get your own pseudo sponsor family and be invited back to their place. Both options are great chances to get out of Chase Hall and be a comfortable environment.
The best thing your DS can do for swab summer is to be as physically fit as possible, make sure all the required documents are complete, and all of the required items are purchased. USCGA has been doing this for a long time - sure, there are always benefits to insider information but it's not necessary. One tip I would recommend is to have your DS write a letter to himself about why he chose USCGA and send it to him with your first batch of letters or care package. He will very likely question whether he wants to be there at least once during swab summer, and definitely at least a couple more times throughout his four years there. The letter is a helpful reminder that comes from him, not from a parent or loved one. Other than that, tell your DS to go in with a positive mindset and with a willingness to help others.
I couldn't help but laugh as I read through what others used to sleep under as a swab - I also used my bathrobe. Despite this year's incoming class being 10 years behind mine

, it looks like some things never change.