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Yes, laptop is issued and part of initial ACE loan. DS won't be allowed to bring his laptop on I-day. Furthermore, they are never allowed to connect a personal computer to the government internet. (only issued laptops can do so). I'm also not aware of any "conversion" to allow connection. Also, keep in mind that plebes don't rate media usage for the entire plebe year. So, any personal wifi laptop usage would likely be limited to time at a sponsors house etc. WiFi connectivity in the wardroom and steerage is for upperclass only.
On I-day he will need his cell phone and charger however. He'll be given instructions of how to package and label them etc. as part of the PTR. They will be taken on I-day, and then given to plebes on the three designated "phone home days" during plebe summer. After plebe summer, Mids will have their phones. How much data he will need is dependent on how much he uses the phone. My mid still uses the data plan that our family shares, which is not unlimited. Agree with kinnem to wait and see before changing data plans.