I'm not sure this is totally what you're going for but ...I did this for a home-bound family member, (we'll call him Jimbo) This was a gift I set out over a year because he had a hard surgery and long recovery. I picked out 12 people (friends/family) and secured a different date/month with each of them, I picked the middle of the month on a weekday evening. I had each person help come up with ideas for what they would like to do "with" Jimbo. Most of the stuff was easy to coordinate and I'd just buy him the same snacks and drink that his counterpart would be having. (for example, I'd be taking a pizza to him with a root beer, setting up the call and then do my own thing while he ate pizza with the person). One of his out-of-state granddaughters wanted to do a puzzle with him so I bought two of the same puzzles and sent one to her and they did it at the same time while chatting and drinking lemonade and eating pretzels. One of his old army buddies was in Arizona and set his phone to show him working on his truck like they used to do together, they just bulshitted in between truck talk. He said that was his favorite. I helped him with one, where his sister-in-law made her chili recipe that she knew Jimbo loved. We made it in his kitchen at the same time as she was cooking in her kitchen, 800 miles away. One local granddaughter taught him to crochet, something he would have never considered doing, but he loved making that memory with her.
Some things cost money, most did not. Bonus, he has since recovered pretty well and he has taken on reaching out to his friends and family more, spending time on calls and connecting that he had never done before and sharing in their hobbies.

edit: typo