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Puppy training during quarantine

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We have been waiting over a year for Oliver. Unfortunately when it was time to take him home we were in the middle of quarantine. We picked him up at 8 weeks old and he is now 14 weeks. I have been watching videos so as of now he knows sit, lay, stay, and off. We are working at potty training and for the most part he having only the occasional pee accidents in the house (like one or two a week but i know this doesn't mean he is potty trained.) At night he sleeps from 9 to 6:30 sometimes 7 in a covered crate with no whining. I think we got really lucky as he is very good during the day with the occasional puppy hyper time in the morning but here is where i need help-

I am going to be going back to work in the next month and he has not been crated during the day regularly. He gets crated when i go on runs or to the store or when i need to go up to the office.I try not to take him everywhere with us because I don't want to cause him to get separation anxiety (which he will play by himself and lay around the house by himself and he doesn't really follow us around unless we are in the kitchen). What should i start doing now to help him get ready for when we are back at work? I did notice today when i was out for an hour his bed was wet (from drool).
Also last piece of information is we will be working from 7:30-4:30 but he will have a puppy sitter (aka our mothers) come from 11 until after 12:30 to hang out with him and let him out until he can stay in the crate longer. Do you think we should keep him in the crate in the bedroom? OR we have another crate with can put in the kitchen and attach it to the play pin?

I am really just looking for help so when we leave he doesn't start regressing. Sorry for all the information i just want to be sure i provide it all to get the best advice. THANK YOU IN ADVANCE.