I agree - - don't count out DS2. Plus, he probably is starting to process that DS2 gets to stay home with mommy while he gets trucked off somewhere else. Might be some sibling rivalry going on. You have to remember the 3 yr old brain doesn't necessarily process stuff as fast as ours does, LOL. We've HAD siblings, so we know what sibling rivalry is and how having sibs affects our life. He's just now learning about it! So at first some of the jealousies might not have occurred to him, but now that DS2 is still here and becoming more interactive (that may be part of it too -- DS2 isn't just a sleepy blob anymore, LOL) DS1 is starting to realize hey! DS2 is home with mommy! Why can't *I* be there too?
I think I'd probably start really emphasizing the perks of being older. Point out all the cool stuff he gets to do at school that babies can't do. Really make a deal out of the papers he brings home, and maybe even show the baby (even tho baby won't notice, LOL!) and brag to little bro about how big bro does such cool things at school. Also, the clinginess is probably more for your benefit. My guess is once school begins and you're gone he's fine. So I think I'd treat him lovingly but without emotion "Mommy loves you! And I know you're going to have a fun day at school. See you soon! *kisses, hugs*".
at bedtime you might do something like tell him that BIG BOYS get an extra story at bedtime! So lengthen out your wind down just a bit -- maybe 5-10 minutes -- to give him some additional 1:1 time and cuddles. Then I think during the day I'd start talking about how babies make mommies and daddies SO TIRED because they don't sleep at night and that you're sooo glad DS1 is so big and sleeps so well! Tell him what a pleasure it is to have a son who just goes to sleep like a big boy instead of a baby who has trouble with sleeping. Really lay it on thick. They totally absorb these messages and it's AMAZING how it changes their behavior. Right now I'm using bedtime stories that I make up about my son to influence his behavior.
I am *astonished* at how well this works because to me these are just thinly veiled messages -- not subliminal at all! I would NEVER fall for such an obvious trick! LOL! But they are young and what we say is gospel, so if we tell them a story about themselves where they are a hero because they eat their veggies, you will see a whole new boy in the morning asking for corn for breakfast!
So you might start telling him 'big boy' stories about himself -- how he has fun at school, how he's so helpful with the baby, how he makes mommy's life easier by being so big at bedtime etc. I know how ridiculous that seems, but it is amazing how ti works. Truly.