Sending a postcard or photo through InmateAid is straightforward. Create an account, add your friend as an inmate by entering their name, inmate ID, and facility, and then go to the Letters or Postcards section to upload a photo or write a message. InmateAid handles the printing and mailing from their office in South Florida. The postcard typically reaches the facility within a day or two through the US Postal Service. After that, it goes through the facility mailroom where staff open and inspect it before handing it out at mail call. That mailroom process varies from one facility to the next, so the total time from sending to him holding it in his hands is usually somewhere between 3 and 7 days.
On the phone calls, the setup depends on which phone carrier the facility uses. Every prison and jail has a contracted phone provider, and the cost and process for reducing call costs varies significantly based on that carrier. InmateAid can give you an honest estimate of whether they can save you money on calls and by how much, but they need to know the specific facility to do that. Let them know where your friend is incarcerated and they will look into the details for you.
Starting with a postcard is a great first step. It is a simple way to let someone know they are being thought of.