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There are services like Rover that can come check on your pet and take them for a walk. It's fairly affordable in my experience. And as for when to say goodbye? If your pup is in pain or isn't enjoying life, look into a service like Peaceful Passage. They come to you and although it's great wrenching to say goodbye, they do a great job.
We went through this with our elderly pup during the height of COVID. Best of luck in whatever choice you make.