Carryon limits, how strictly enforced?

Hey everyone,
Bear with me... this is a long email... thanks in advance for the help.
I just did a packing dry run for our trip with my husband and I and our 16 month old and there's NO WAY we can get our carry on bags to under 13 pounds each.
With snacks and toys for the flight, a few changes of outfits, a dozen or so nappies, our toiletries, and enough Children's Advil to get through the latest teething spell, PLUS a 2 pound cd player that we don't want to check, it seems like our carryons are way over the limit. We have plenty of luggage to check, and we've whittled our hand baggage to literally what we'd need for 48 hours of travel in case some or all of our luggage went missing or we got delayed. But I'm finding th 13 pound limit totally insanse. Our bags are TINY, they're just heavy.
How flexible do you think they'll be with us... considering we're travelling with a toddler in Premium Economy. Here's an overview of what we're bringing and the approx. weights of each carryon:
-husband's carryon has come in at a whopping 17 pounds (and it's a tiny carry on from Eagle Creek) but he's holding on to the toiletries and the baby's meds
-my carryon is about 15 pounds with my face cremes and a few changes of tshirts
-the baby's carryon/diaper bag/stuff for the flight bag is a small duffel bag that slightly exceeds the dimensional requirements but it's still small... and it's about 16 pounds. It includes things for the flight, though, like snacks, her lunch, diapers, toys, etc. We deliberately left this one not full to the brim so it can technically be squished down to fit the dimensional limit. Depending on who I have spoken to at Virgin, I've been told that the baby gets a) no carry on, b) a carryon like any other passenger, and c) only a diaper bag. So I'm going to play dumb, call this duffel her "diaper bag" that includes her snacks for the flight, and smile a lot at the agent, hoping she'll allow it on.
-in addition, I'm bringing a small backpack that I'm hoping will qualify as my "purse" since I don't usually carry a purse when travelling... something for a book and a camera and my earplugs, etc. This has certainlly always worked for me on Air France and Alitalia.
-in addition, we will have a small Maclaren umbrella stroller that I'm hoping they'll allow me to wheel to the gate and bring on the plane, or at least put somewhere so that it's there at the gate when we land. Is this called "gate check"? Will they allow it? I can't imagine having to check a stroller and retrieve it at the carousel, but the way the website it worded it implies that's what they do.
-and finally, we'll also have a backpack carrier (lightweight aluminum frame) which I don't want to check because I don't want it to get damaged going through a luggage carousel. Are we pushing our luck to ask if we can bring it to the gate... would it help if we wear her in it at the gate so they can see why we want it on the plane with us?
Hoping they'll cut us a little slack... my brother in law just flew this leg in economy with his toddler and he recalls seeing many many people bring on much larger carryons than he did. But then again, I've also heard from other travellers that they might weigh it and force me to check it.
Thanks for any insight you can provide,
~kat
Edited to cut out the fluff, get to the point, and not bog you all down with so much to read.
Bear with me... this is a long email... thanks in advance for the help.

I just did a packing dry run for our trip with my husband and I and our 16 month old and there's NO WAY we can get our carry on bags to under 13 pounds each.
With snacks and toys for the flight, a few changes of outfits, a dozen or so nappies, our toiletries, and enough Children's Advil to get through the latest teething spell, PLUS a 2 pound cd player that we don't want to check, it seems like our carryons are way over the limit. We have plenty of luggage to check, and we've whittled our hand baggage to literally what we'd need for 48 hours of travel in case some or all of our luggage went missing or we got delayed. But I'm finding th 13 pound limit totally insanse. Our bags are TINY, they're just heavy.
How flexible do you think they'll be with us... considering we're travelling with a toddler in Premium Economy. Here's an overview of what we're bringing and the approx. weights of each carryon:
-husband's carryon has come in at a whopping 17 pounds (and it's a tiny carry on from Eagle Creek) but he's holding on to the toiletries and the baby's meds
-my carryon is about 15 pounds with my face cremes and a few changes of tshirts
-the baby's carryon/diaper bag/stuff for the flight bag is a small duffel bag that slightly exceeds the dimensional requirements but it's still small... and it's about 16 pounds. It includes things for the flight, though, like snacks, her lunch, diapers, toys, etc. We deliberately left this one not full to the brim so it can technically be squished down to fit the dimensional limit. Depending on who I have spoken to at Virgin, I've been told that the baby gets a) no carry on, b) a carryon like any other passenger, and c) only a diaper bag. So I'm going to play dumb, call this duffel her "diaper bag" that includes her snacks for the flight, and smile a lot at the agent, hoping she'll allow it on.
-in addition, I'm bringing a small backpack that I'm hoping will qualify as my "purse" since I don't usually carry a purse when travelling... something for a book and a camera and my earplugs, etc. This has certainlly always worked for me on Air France and Alitalia.
-in addition, we will have a small Maclaren umbrella stroller that I'm hoping they'll allow me to wheel to the gate and bring on the plane, or at least put somewhere so that it's there at the gate when we land. Is this called "gate check"? Will they allow it? I can't imagine having to check a stroller and retrieve it at the carousel, but the way the website it worded it implies that's what they do.
-and finally, we'll also have a backpack carrier (lightweight aluminum frame) which I don't want to check because I don't want it to get damaged going through a luggage carousel. Are we pushing our luck to ask if we can bring it to the gate... would it help if we wear her in it at the gate so they can see why we want it on the plane with us?
Hoping they'll cut us a little slack... my brother in law just flew this leg in economy with his toddler and he recalls seeing many many people bring on much larger carryons than he did. But then again, I've also heard from other travellers that they might weigh it and force me to check it.
Thanks for any insight you can provide,
~kat
Edited to cut out the fluff, get to the point, and not bog you all down with so much to read.
