First time puppy owner with crate-trained but anxious / stressed puppy

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My puppy whines constantly when alone and I'm having trouble figuring out if this is normal puppy whining behavior and I should ignore it, or if it's the beginnings of separation anxiety. We have consulted a trainer (and are working with her on other behaviors) but she has ZERO experience raising puppies so it's hard to take her advice seriously for separation anxiety. I'm also looking into a different trainer to work on separation anxiety since it is starting take a major toll on both my husband and myself. I also am concerned I (and/or my husband) are making the separation anxiety worse since we are home almost all the time or we hire someone to be with him.

Our puppy is about fourteen weeks old and crate trained and he is perfectly happy in the crate IF he can see someone is in the room. He loves his crate so no issues with crate training. We have tried the game of gradually leaving for five seconds and returning but it seems we are not making much progress (we also reset the time if he starts whining or stop the exercise completely and resuming later). Sometimes he is fine if we leave for a minute (rare but great occurrence!) and some days he is not ok with us even heading towards the door. We leave him a special snack or a stuffed kong when we leave (to go to other room) but he still freaks out as soon as he's done with it. He gets plenty of exercise of during the day and night and we only crate him when he is tired / calm / mellow (after exercise, feeding and potty). We also wait until he's settled in the crate before trying to leave but it's not working.

My husband and I also give him treats when we do any activities associated with leaving (keys jingling, putting on our jackets).

Should we just ignore his whining and try to leave for five minutes? or should we continue the gradual (albeit extremely slow) method of leaving him for a few seconds at a time (or right before his threshold)?

Also if he's ok with being left alone for a minute (one time), is that his new threshold? or is it only up until the point of whining at any given time?

Any advice, thoughts and suggestions are appreciated. I'd be so thankful if we could leave him alone even for ten minutes.

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